(1R,2S,3S,5R)-(-)-2-bromo-3-hydroxy-bicyclo[3.2.0]heptan-6-one | 73346-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3S,5R)-(-)-2-bromo-3-hydroxy-bicyclo[3.2.0]heptan-6-one
• 英文别名: (1α,2α,3β, 5α)-2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one；(1α,2α,3β,5α)-2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one；(1R,2S,3S,5R)-2-Bromo-3-hydroxybicyclo[3.2.0]heptan-6-one
• CAS: 73346-97-1
• 化学式: C₇H₉BrO₂
• 分子量: 205.051
• InChiKey: PZDPQFNHGDOCGG-SOWDYBQPSA-N

物化性质

• 沸点：
  319.1±42.0 °C(Predicted)
• 密度：
  1.813±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,5R)-(-)-2-bromo-3-hydroxy-bicyclo[3.2.0]heptan-6-one 在 对甲苯磺酸 作用下， 以 乙二醇 、 苯 为溶剂， 生成 (1'R,2'S,3'S,5'R)-2'-bromospiro[1,3-dioxolane-2,6'-bicyclo[3.2.0]heptane]-3'-ol
  参考文献：
  名称：

  Novel prostaglandin intermediates

  摘要：

  该发明涉及(1.alpha.，2.alpha.，4.alpha.，6.alpha.)-3-氧杂三环[4.2.0.0.sup.2,4]辛酮-7-酮及其衍生物，其中酮基受保护，这些化合物是制备天然和合成前列腺素的有用中间体。描述和举例了制备这些化合物的方法，以及它们转化为已知前列腺素中间体的方法。

  公开号：

  US04272629A1
• 作为产物：
  描述：

  4',5'-bis(benzyloxymethyl)bicyclo<3.2.0>hept-2-ene-6-spiro-2'-(1',3'-dioxolane) 在 硫酸 、 N-溴代乙酰胺 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 (1R,2S,3S,5R)-(-)-2-bromo-3-hydroxy-bicyclo[3.2.0]heptan-6-one
  参考文献：
  名称：

  Kanger, T. P.; Kabat, M.; Vikha, E., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 8, p. 1481 - 1484

  摘要：

  DOI：

文献信息

• METHOD FOR MANUFACTURING ESTER
  申请人：Ishihara Kazuaki

  公开号：US20130217898A1

  公开（公告）日：2013-08-22

  The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr 4 ) n , which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF 3 C 6 H 3 ) 4 ] 2 was used as the catalyst, ε-caprolactone was obtained at an isolated yield of 82%.

  本发明涉及一种从酮或醛（作为反应底物）制造酯的方法，该方法通过使用过氧化氢进行巴耶-维利格氧化反应，在该方法中，作为催化剂使用了M(BAr4)n，该催化剂是一种金属硼酸盐（M代表碱金属或碱土金属；Ar代表芳基；n与M的化合价相同）。例如，当环己酮作为反应底物，Sr[B(3,5-CF3C6H3)4]2作为催化剂时，得到了ε-己内酯，其分离收率为82%。
• Reduction of bicyclo [3.2.0] hept-2-en-6-one with dehydrogenase enzymes in whole cell preparations of some fungi and yeasts
  作者：Michael J. Dawson、Gordon C. Lawrence、Gerald Lilley、Martin Todd、David Noble、Susan M. Green、Stanley M. Roberts、Timothy W. Wallace、Roger F. Newton、Malcolm C. Carter、Peter Hallett、John Paton、Derek P. Reynolds、Stuart Young

  DOI：10.1039/p19830002119

  日期：——

  (±)-Bicyclo [3.2.0] hept-2-en-6-one (1) was reduced using a variety of fungi and yeasts. Bakers' yeast gave 6-exo-(1R,5S,6S)-bicyclo [3.2.0] hept-2-en-6-ol (2a) and 6-endo-(1S,5R,6S)-bicyclo[3.2.0]-hept-2-en-6-ol (3b) while Curvularia lunata and Mortierella ramanniana gave only the 6-endo-alcohol (3b) and optically active bicycloheptenone (1a). Under slightly modified reaction conditions (±)-6-endo-bicyclo

  （±）-Bicyclo [3.2.0] hept-2-en-6-one（1）使用多种真菌和酵母还原。面包酵母产生6- exo-（1 R，5 S，6 S）-双环[3.2.0] hept-2-en-6-ol（2a）和6- endo-（1 S，5 R，6 S）-双环[3.2.0]-庚-2-en-6-ol（3b），而Curvularia lunata和Mortierella ramanniana仅产生6-内醇（3b）和旋光性双环庚烯酮（1a）。在稍微改变的反应条件下，（±）-6-内-双环[3.2.0]庚-2-烯-6-醇被面包酵母氧化，得到（1 S，5 R）-双环[3.2.0] hept-2-en-6-one（1b）和内醇（3a）。
• Enantio-complementary total asymmetric syntheses of prostaglandin E2 and prostaglandin F2?
  作者：John Davies、Stanley M. Roberts、Derek P. Reynolds、Roger F. Newton

  DOI：10.1039/p19810001317

  日期：——

  bromohydrins (–)-(9) and (+)-(9). The bromohydrin (–)-(9) was converted into prostaglandin E2(1) and prostaglandin F2α(2) by reaction of the chiral cuprate reagent (15) with the tricyclic ketone (10), while the bromohydrin (+)-(9) was converted into the prostaglandins by reaction of the epoxyacetal (11) with the same cuprate reagent (15).

  使用积极发酵的酵母将外消旋酮（6）转化为非对映异构醇（7）和（8）。将这些醇分离并转化为溴代醇（-）-（9）和（+）-（9）。通过手性铜酸盐试剂（15）与三环酮（10）反应，将溴代醇（-）-（9）转化为前列腺素E 2（1）和前列腺素F2α（2），而溴代醇（+）- （9）通过环氧乙缩醛（11）与相同的铜酸盐试剂（15）反应而转化为前列腺素。
• Chemoenzymatic synthesis of a novel ligand for rhodium-catalysed asymmetric hydrogenation
  作者：Brian Adger、Ulrich Berens、Matthew J. Griffiths、Michael J.K elly、Ray McCague、John A. Miller、Christopher F. Palmer、Stanley M. Roberts、Rüdiger Selke、Ute Vitinius、Guy Ward

  DOI：10.1039/a704136e

  日期：——

  The hydrogenation of alkenes 7a–g using a chiral rhodium catalyst 6 (based on a bicyclo[3.2.0]heptane framework) takes place to give the phenylalanine derivatives 8a–g with remarkably high stereoselectivity (59–92% ee).

  使用手性铑催化剂 6（基于双环[3.2.0]庚烷框架）对烯烃 7a-g 进行氢化反应，得到苯丙氨酸衍生物 8a-g，其立体选择性极高（59-92% ee）。
• Bicyclo[2.2.1]hept-7-ylamine Derivatives and Their Uses
  申请人：Finch Harry

  公开号：US20100144852A1

  公开（公告）日：2010-06-10

  Compounds of formula (I) have muscarinic M3 receptor modulating activity; Formula (I) wherein A is an oxygen atom or group —N(R 12 )—; (i) R 1 is C 1 -C 6 -alkyl or a hydrogen atom; and R 2 is a hydrogen atom or a group —R 5 , —Z—Y—R 5 —Z—NR 9 R 10 ; —Z—CO—NR 9 R 10 ; —Z—NR 9 —CO—R 5 ; or —Z—CO 2 H; and R 3 is a lone pair, or C 1 -C 6 -alkyl in which case the nitrogen atom to which it is attached is a quaternary nitrogen and carries a positive charge; or (ii) R 1 and R 3 together with the nitrogen to which they are attached form a heterocycloalkyl ring, and R 2 is a hydrogen atom; or a group —R 5 , —Z—Y—R 5 , —Z—NR 9 R 10 , —Z—CO—NR 9 R 10 , —Z—NR 9 —CO—R 5 , or —Z—CO 2 H, in which cases the nitrogen atom to which it is attached is a quaternary nitrogen and carries a positive charge; or (iii) R 1 and R 2 together with the nitrogen to which they are attached form a heterocycloalkyl ring, said ring being substituted by a group —Y—R 5 , —Z—Y—R 5 , —Z—NR 9 R 10 ; —Z—CO—NR 9 R 10 ; —Z—NR 9 —CO—R 5 ; or —Z—CO 2 H and R 3 is a lone pair, or C 1 -C 6 -alkyl in which case the nitrogen atom to which it is attached is a quaternary nitrogen and carries a positive charge; R 4 is a group of formula (a), (b), (c) or (d); is an C 1 -C 6 -alkyl, aryl, aryl-fused-cycloalkyl, aryl-fused-heterocycloalkyl, heteroaryl, aryl(C 1 -C 8 -alkyl)-, heteroaryl(C 1 -C 8 -alkyl)-, cycloalkyl or heterocycloalkyl group, and the remaining variables are as defined in the specification.

  式(I)的化合物具有肌动蛋白M3受体调节活性；其中A是氧原子或基团-N(R12)-; (i) R1是C1-C6-烷基或氢原子；R2是氢原子或基团-R5、-Z-Y-R5-Z-NR9R10、-Z-CO-NR9R10、-Z-NR9-CO-R5或-Z-CO2H；R3是孤对电子，或C1-C6-烷基，此时它连接的氮原子是季铵氮并带有正电荷；或者(ii) R1和R3与它们连接的氮形成杂环烷基环，R2是氢原子；或者是一个基团-R5、-Z-Y-R5、-Z-NR9R10、-Z-CO-NR9R10、-Z-NR9-CO-R5或-Z-CO2H，此时连接它的氮原子是季铵氮并带有正电荷；或者(iii) R1和R2与它们连接的氮形成杂环烷基环，所述环被基团-Y-R5、-Z-Y-R5、-Z-NR9R10、-Z-CO-NR9R10、-Z-NR9-CO-R5或-Z-CO2H取代，R3是孤对电子，或C1-C6-烷基，此时连接它的氮原子是季铵氮并带有正电荷；R4是式(a)、(b)、(c)或(d)的基团；是C1-C6-烷基、芳基、芳基融合环烷基、芳基融合杂环烷基、杂环芳基、芳基(C1-C8-烷基)-、杂环芳基(C1-C8-烷基)-、环烷基或杂环烷基基团，其余变量如说明书所定义。