3-bromo-3-butenyl tert-butyldiohenylsilyl ether | 144543-35-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-bromo-3-butenyl tert-butyldiohenylsilyl ether
• 英文别名: 2-bromo-4-tert-butyldiphenylsilyloxybutene；((3-bromobut-3-en-1-yl)oxy)(tert-butyl)diphenylsilane；(3-bromobut-3-enyloxy)(tert-butyl)diphenylsilane；[(3-bromo-3-buten-1-yl)oxy](1,1-dimethylethyl)diphenylsilane；3-bromobut-3-enoxy-tert-butyl-diphenylsilane
• CAS: 144543-35-1
• 化学式: C₂₀H₂₅BrOSi
• 分子量: 389.407
• InChiKey: BCZMRVNGRDCQDU-UHFFFAOYSA-N

物化性质

• 沸点：
  398.8±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-3-butenyl tert-butyldiohenylsilyl ether 在 sodium tetrahydroborate 、 叔丁基锂 作用下， 以 乙醇 为溶剂， 反应 4.08h， 生成 1-丁醇,4-[[(1,1-二甲基乙基)二苯基甲硅烷基]氧代]-2-亚甲基-
  参考文献：
  名称：

  Myers, Andrew G.; Dragovich, Peter S.; Kuo, Elaine Y., Journal of the American Chemical Society, 1992, vol. 114, # 24, p. 9369 - 9386

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴-3-丁烯醇 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到3-bromo-3-butenyl tert-butyldiohenylsilyl ether
  参考文献：
  名称：

  Synthesis of Highly Substituted Symmetrical 1,3-Dienes via Organocuprate Oxidation

  摘要：

  由烯基卤化物形成的烯基有机铜酸盐发生氧化反应，可生成高度取代的对称 1,3 二烯。由有机锂和格氏试剂形成的铜酸盐也可以耐受，而且反应进行时烯基的几何形状得以保留。

  DOI：

  10.1055/s-0031-1290116

文献信息

• Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition–Polar Cyclization Cascade
  作者：Chao Shu、Riccardo S. Mega、Björn J. Andreassen、Adam Noble、Varinder K. Aggarwal

  DOI：10.1002/anie.201808598

  日期：2018.11.19

  Herein, we describe the development of a photoredox‐catalyzed decarboxylative radical addition–polar cyclization cascade approach to functionalized cyclopropanes. Reductive termination of radical–polar crossover reactions between aliphatic carboxylic acids and electron‐deficient alkenes yielded carbanion intermediates that were intercepted in intramolecular alkylations with alkyl chlorides appended

  在此，我们描述了光氧化还原催化的脱羧自由基加成-极性环化级联方法对功能化环丙烷的开发。脂肪族羧酸和缺电子烯烃之间的自由基-极性交叉反应的还原终止产生了碳负离子中间体，该碳负离子中间体在分子内烷基化中被附加到烯烃底物上的烷基氯拦截。温和的条件利用了现成的有机光催化剂和可见光，被证明适用于多种结构复杂的羧酸和多种氯烷基烯烃，表现出出色的官能团耐受性。
• The first synthetic studies on pestalotiopsin A. A stereocontrolled approach to the functionalised bicyclic coreElectronic supplementary information (ESI) available: crystal structure analysis of 18a. See http://www.rsc.org/suppdata/ob/b2/b209066j/
  作者：Derek Johnston、Emmanuel Couché、David J. Edmonds、Kenneth W. Muir、David J. Procter

  DOI：10.1039/b209066j

  日期：2003.1.13

  structurally unique, caryophyllene-type sesquiterpene which has shown immunosuppressive activity and cytotoxicity in preliminary assays. A stereocontrolled approach to the functionalised 2-oxabicyclo[3.2.0]-heptane core of pestalotiopsin A is described. This constitutes the first synthetic studies on pestalotiopsin A. Our approach includes a samarium(II)-mediated 4-exo-trig cyclisation and a trans-lactonisation

  骨视蛋白A是一种结构独特的，石竹烯型倍半萜，在初步试验中显示出免疫抑制活性和细胞毒性。描述了一种立体控制的方法来合成鼠疫视蛋白A的2-氧杂双环[3.2.0]-庚烷核心。这构成了对瘟疫菌素A的首次合成研究。我们的方法包括includes（II）介导的4-exo-trig环化和通过向环丁酮中间体中添加烷基y试剂而引发的反式内酯化过程。进一步的操作提供了进入高级中间体的途径，这些中间体是未来构建靶最终环的极好前体。
• A new ground state single electron donor for excess electron transfer studies in DNA
  作者：Christian Trindler、Antonio Manetto、Jürgen Eirich、Thomas Carell

  DOI：10.1039/b906180k

  日期：——

  A new photoinducible single electron donor has been developed, which, when linked to thymidine, is shown to be an efficient ground state reducing agent in DNA; the donor can be activated at wavelengths where standard DNA does not absorb.

  一种新的可光诱导单电子供体已被开发，当其与胸苷连接时，显示出在DNA中作为有效的基态还原剂；该供体可以在标准DNA不吸收的波长下被激活。
• CHEMICAL COMPOUNDS
  申请人：Di Fabio Romano

  公开号：US20080114049A1

  公开（公告）日：2008-05-15

  The present invention relates to (1S,6R)-6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptane, pharmaceutically acceptable salts, prodrugs or solvates thereof; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as serotonin (5-HT), dopamine (DA) and norepinephrine (NE), re-uptake inhibitors.

  本发明涉及(1S,6R)-6-(3,4-二氯苯基)-1-[(甲氧基)甲基]-3-氮杂双环[4.1.0]庚烷，其药学上可接受的盐、前药或溶剂化物；用于其制备的中间体，含有它们的制药组合物以及它们在治疗中的应用，作为5-羟色胺(5-HT)、多巴胺(DA)和去甲肾上腺素(NE)的再摄取抑制剂。
• AZABICYCLIC COMPOUNDS AS INHIBITORS OF MONOAMINES REUPTAKE
  申请人：Bertani Barbara

  公开号：US20100035914A1

  公开（公告）日：2010-02-11

  The present invention relates to novel compounds of formula (I)′, and pharmaceutically acceptable salts, prodrugs or solvates thereof: wherein R 1 is hydrogen or C 1-4 alkyl; R 2 is a group A, K or W wherein A is K is an α or β naphthyl group, optionally substituted by 1 or 2 groups R 18 , each of them being the same or different; and W is and wherein G is a 5,6-membered monocyclic heteroaryl group, or a 8- to 11-membered heteroaryl bicyclic group; wherein G may be substituted by (R 15 ) p , which can be the same or different; p is an integer from 0 to 5; R 3 is selected from the group consisting of: hydrogen, fluorine, and C 1-4 alkyl; or corresponds to a group X or X 1 ; R 4 is selected from the group consisting of: hydrogen, fluorine, and C 1-4 alkyl; or corresponds to a group X or X 1 ; R 5 is hydrogen or C 1-4 alkyl; R 7 is hydrogen or C 1-4 alkyl; or is a group X, X 1 , X 2 or X 3 ; wherein X is X 1 is X 2 is and X 3 is R 6 is hydrogen or C 1-4 alkyl; or is a group X or X 1 ; R 9 is C 1-4 alkyl; R 10 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 8 is a 5-6 membered heterocycle group, which may be substituted by one or two substituents selected from the group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy and C 1-4 alkanoyl; R 11 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 12 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 13 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 14 is selected from the group consisting of: hydrogen, halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 15 is selected from the group consisting of: halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 8 ; R 16 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkylC 1-3 alkyl; R 17 is hydrogen or C 1-4 alkyl; R 18 is selected from the group consisting of: halogen, cyano, and C 1-4 alkyl; R 19 is haloC 1-2 alkyl; and n is 1 or 2; with the proviso that: if R 2 is A, R 3 , R 4 , R 5 , R 6 , R 7 , R 10 , R 11 , R 13 , and R 14 are hydrogen, and R 12 is fluorine, R 1 is C 1-4 alkyl; if R 2 is A, R 3 , R 4 , R 5 , R 6 , R 7 , R 10 , R 11 , R 13 , and R 14 are hydrogen, and R 1 is methyl, R 12 is halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl or SF 5 ; or corresponds to a group R 8 ; and processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as serotonin (5-HT), dopamine (DA) and norepinephrine (NE), re-uptake inhibitors.

  本发明涉及式(I)'的新化合物，以及其药学上可接受的盐、前药或溶剂化物： 其中， R1为氢或C1-4烷基； R2为A、K或W基团，其中 A为 K为α或β萘基团，可选地被1或2个R18基团取代，每个基团相同或不同； W为 其中， G为5,6-成员单环杂芳基团或8-至11-成员杂芳双环基团；其中G可能被(R15)p取代，其中p可以是0到5的整数；R3选择自氢、氟和C1-4烷基；或对应于X或X1基团； R4选择自氢、氟和C1-4烷基；或对应于X或X1基团； R5为氢或C1-4烷基； R7为氢或C1-4烷基；或为X、X1、X2或X3基团； 其中， X为 X1为 X2为 且X3为 R6为氢或C1-4烷基；或为X或X1基团； R9为C1-4烷基； R10选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R8为5-6成员杂环基团，可以被来自卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基和C1-4酰基的一或两个取代基团取代； R11选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R12选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R13选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R14选择自氢、卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R15选择自卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基和SF5；或对应于R8基团； R16为氢、C1-4烷基、C3-6环烷基或C3-6环烷基C1-3烷基； R17为氢或C1-4烷基； R18选择自卤素、氰基和C1-4烷基； R19为卤代C1-2烷基；且 n为1或2； 但前提是，如果R2为A，R3、R4、R5、R6、R7、R10、R11、R13和R14为氢，而R12为氟，R1为C1-4烷基；如果R2为A，R3、R4、R5、R6、R7、R10、R11、R13和R14为氢，而R1为甲基，R12为卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基或SF5；或对应于R8基团；以及用于制备它们的过程、用于这些过程的中间体、含有它们的制药组合物以及它们在治疗中的应用，作为5-羟色胺（5-HT）、多巴胺（DA）和去甲肾上腺素（NE）的再摄取抑制剂。