(E)-hept-1-en-1-yl-1,3,2-benzodioxaborole | 98631-59-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (E)-hept-1-en-1-yl-1,3,2-benzodioxaborole
• 英文别名: E-1-heptenylcatecholborane；2-[(E)-hept-1-enyl]-1,3,2-benzodioxaborole
• CAS: 98631-59-5
• 化学式: C₁₃H₁₇BO₂
• 分子量: 216.088
• InChiKey: UTHBKPMJVTZQEW-DHZHZOJOSA-N

物化性质

• 沸点：
  100-104 °C(Press: 0.3 Torr)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-hept-1-en-1-yl-1,3,2-benzodioxaborole 在 水 作用下， 反应 1.0h， 以90%的产率得到E-庚烯-1-基硼酸
  参考文献：
  名称：

  2-Pyrones possessing antimicrobial and cytotoxic activities

  摘要：

  The 2-pyrone sub-unit is found in a number of natural products possessing broad spectrum biological activity. Such compounds are validated as being capable of binding to specific protein domains and able to exert a remarkable range of biological effects. In an effort to identify synthetic 2-pyrones with interesting biological effects, herein we report the synthesis and biological evaluation of 4-substituted-6-methyl-2-pyrones. Synthetic routes to 4-alkyl/alkenyl/aryl/alkynyl-6-methyl-2-pyrones have been developed utilising Sonogashira, Suzuki and Negishi cross-coupling starting from readily available 4-bromo-6-methyl-2-pyrone. Specific conditions for each organometallic protocol were required for successful cross-coupling. In particular, a triethylamine/acetonitrile-base/solvent mixture was crucial to Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone, whereas thallium carbonate was a mandatory base for the Suzuki cross-coupling of trialkylboranes. The 2-pyrones demonstrate potent inhibitory activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Schizosaccharomyces pombe and Botrytis cinerea. The growth inhibitory activities of selected 2-pyrones were determined in A2780 human ovarian carcinoma and K562 human chronic myelogenous leukaemia cell lines using an in vitro cell culture system (MTT assay). These studies demonstrate that 4-phenylethynyl-, 4-tetrahydropyranylpropargyl ether- and 4-ethynyl-6-methyl-2-pyrones have excellent potential as a new class of anticancer agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.051
• 作为产物：
  描述：

  1-庚炔 在 儿萘酚硼烷 作用下， 生成 (E)-hept-1-en-1-yl-1,3,2-benzodioxaborole
  参考文献：
  名称：

  Trans-olefin compounds, method for production thereof, liquid crystal

  摘要：

  本发明涉及一种由通式（1）表示的反式烯烃化合物，作为液晶组分的成分有用，作为杀虫剂、药物、液晶材料等的中间体有用的反式烯烃化合物，用于生产这些反式烯烃化合物的方法，含有该反式烯烃化合物作为活性成分的液晶组合物，以及使用该液晶组合物的液晶元件。在通式（1）中，R.sup.1、A.sup.1、A.sup.2、A.sup.3、Z和R.sup.2与规范中定义的相同。此外，m、p、q、n、r、s和t分别是规范中定义的整数。

  公开号：

  US06030546A1
• 作为试剂：
  描述：

  正戊基溴化镁 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 四(三苯基膦)钯 、 (E)-hept-1-en-1-yl-1,3,2-benzodioxaborole 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (1E,4E)-3-pentyl-1-phenyl-1,4-decadiene
  参考文献：
  名称：

  Nickel-Catalyzed Coupling Reaction of 1,3-Disubstituted Secondary Allylic Carbonates and Lithium Aryl- and Alkenylborates

  摘要：

  This account describes coupling reaction of 1,3-disubstituted secondary allylic carbonates with lithium aryl- and alkenylborates in the presence of a nickel. catalyst. Berates examined are 4, 5, and 6, and reactivity and selectivity were investigated using the allylic carbonates la and Ib. Coupling of la,b with berates 4 was effected with the nickel catalyst, NiCl2(PPh(3))(2) or NiCl2(dppf), in THF at 45-65 degrees C to provide products 3 in good yields with almost 100% regio- and stereoselectivities. Trivalent organoboranes prepared from acetylenes by hydroboration with catecholborane also underwent coupling reaction with la,b after transformation to berates 5 with MeLi. Though coupling using 4 and 5 required elevated temperature (45-65 degrees C), cyclic berates 6 prepared in situ from boronates 8 and MeLi were found to couple with la,b at room temperature or below. Regio- and stereoselectivities were almost 100% as were observed in the cases of 4 and 5. In these reactions, palladium complexes such as Pd(PPh(3))(4), Pd-2(dba)(3) . CHCl3 + 2 PPh(3) showed no catalytic activity. Stereochemical aspect of the present reaction was studied using cyclohexenyl carbonate 24 with 2-furylborate 4e and phenylborate 6a, and was found to proceed with overall anti fashion. With additional experiments, the mechanism of the present reaction was discussed in terms of transient pi-allylnickel intermediates.

  DOI：

  10.1021/jo960458c

文献信息

• Diphenylacetylene compound, process for preparing the same and liquid
  申请人：Sumitomo Chemical Company, Limited

  公开号：US05658489A1

  公开（公告）日：1997-08-19

  A diphenylacetylene compound of the formula [1]: ##STR1## wherein R is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.16 alkoxyalkyl group; X.sup.1, X.sup.2, X.sup.3, X.sup.4, Y.sup.1, Y.sup.2, Y.sup.3 and Y.sup.4 are independently from each other a --CH-- group, a --CF-- group or a nitrogen atom; A is a hydrogen atom, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, a 4-R.sup.1 -(cycloalkyl) group, 4-R.sup.1 -(cycloalkenyl) group or a R.sup.1 --(O).sub.m group in which R.sup.1 is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.12 alkynyl group; and m is 0 or 1, which has an excellent anisotropy of refractive index and a low viscosity and is useful as a component of a liquid crystal composition.

  一种二苯基炔化合物，其化学式为[1]: ##STR1## 其中，R为C1-C12烷基、C2-C12烯基或C2-C16氧烷基；X1、X2、X3、X4、Y1、Y2、Y3和Y4各自独立为--CH--基团、--CF--基团或氮原子；A为氢原子、氟原子、三氟甲基、三氟甲氧基、氰基、4-R1-(环烷基)基团、4-R1-(环烯基)基团或R1--(O)m基团，其中R1为C1-C12烷基、C2-C12烯基或C2-C12炔基；m为0或1，具有优异的折射率各向异性和低粘度，可用作液晶组合物的组分。
• Rhodium-catalyzed asymmetric 1,4-addition of 2-alkenyl-1,3,2-benzodioxaboroles to α,β-unsaturated ketones
  作者：Yoshiaki Takaya、Masamichi Ogasawara、Tamio Hayashi

  DOI：10.1016/s0040-4039(98)01866-8

  日期：1998.11

  with catecholborane, with α,β-unsaturated ketones in the presence of catalyst and triethylamine in proceeded with high enantioselectivity at 100 °C to give high yields of optically active β-alkenyl ketones of over 90% ee. One pot synthesis of the 1,4-addition product is also successful in the rhodium-catalyzed asymmetric reaction by use of alkenylboranes generated in situ from alkyne and catecholborane

  在催化剂和三乙胺的存在下，炔烃与儿茶酚硼烷的硼氢化反应容易制得的2-烯基-1,3,2-苯并二恶杂硼酸酯与α，β-不饱和酮的反应在100°C下以高对映选择性进行ee超过90％ee的高光学活性β-烯基酮收率。通过使用从炔烃和儿茶酚硼烷原位生成的烯基硼烷，在铑催化的不对称反应中也成功完成了1,4-加成产物的一锅合成。
• The Reactions of Copper(I) 1-Alkenyltrimethylborates with Allylic Bromides or 2-Propynyl Bromide
  作者：Norio Miyaura、Takashi Yano、Akira Suzuki

  DOI：10.1246/bcsj.53.1471

  日期：1980.5

  The reactions between copper(I) 1-alkenyltrimethylborates (readily obtainable from 2-(1-alkenyl)-1,3,2-benzodioxaboroles and methyllithium) and allylic bromides or 2-propynyl bromide were found to give corresponding coupling products. These reactions provide new synthetic routes to 1,4-alkadienes or 1,2,7-alkatrien-5-ynes.

  发现铜 (I) 1-烯基三甲基硼酸盐（可容易地从 2-(1-烯基)-1,3,2-苯并二氧杂环戊烷和甲基锂获得）与烯丙基溴或 2-丙炔基溴之间的反应得到相应的偶联产物。这些反应为 1,4-二烯烃或 1,2,7-烷三烯-5-炔提供了新的合成路线。
• An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone
  作者：Lester R. Marrison、Julia M. Dickinson、Razwan Ahmed、Ian J.S. Fairlamb

  DOI：10.1016/s0040-4039(02)02207-4

  日期：2002.12

  We herein report the efficient syntheses of biologically active 4-alkenyl- and 4-alkynyl-6-methyl-2-pyrones using Pd-catalysed coupling procedures. A palladium on carbon/triphenylphosphine combination is shown to be the most effective catalyst for Sonogashira cross-coupling of several terminal acetylenes with 4-bromo-6-methyl-2-pyrone in yields of up to 95%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Suzuki cross-coupling approaches to the synthesis of bioactive 3-substituted and 5-substituted-4-methoxy-6-methyl-2-pyrones
  作者：Lester R. Marrison、Julia M. Dickinson、Ian J.S. Fairlamb

  DOI：10.1016/s0960-894x(03)00546-8

  日期：2003.8

  Suzuki cross-coupling has been used to access a wide range of 3- and 5-substituted 2-pyrones, which show remarkable inhibitory activity against bacteria, yeasts and fungi. 3-Octenyl and 5-octenyl 2-pyrones inhibit human ovarium carcinoma (A2780) and human chronic myelogenous leukaemia (K562) cell lines at the micromolar level. (C) 2003 Elsevier Ltd. All rights reserved.