(E)-pent-1-en-1-yl-1,3,2-benzodioxaborole | 37494-02-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (E)-pent-1-en-1-yl-1,3,2-benzodioxaborole
• 英文别名: [(E)-1-pentenyl]-1,3,2-benzodioxaborole；(E)-1-pentenyl-1,3,2-benzodioxaborole；2-pent-1-en-t-yl-benzo[1,3,2]dioxaborole；E-1-pentenyl-catecholborane；2-<(E)-1-Penten-1-yl>-1,3,2-benzodioxaborol；2-[(E)-pent-1-enyl]-1,3,2-benzodioxaborole
• CAS: 37494-02-3
• 化学式: C₁₁H₁₃BO₂
• 分子量: 188.034
• InChiKey: QVMPTJREUYDXBG-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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)-pent-1-en-1-yl-1,3,2-benzodioxaborole 在 sodium hydroxide 、 水 、 碘 作用下， 生成 (E)-1-iodo-1-pentene
  参考文献：
  名称：

  信息素bombykol及其三个几何异构体的立体定向合成

  摘要：

  通过在碱的存在下合适的烯基硼烷和烯基卤化物之间的钯催化的交叉偶联反应，可以实现信息素孟皮酚及其三种几何异构体的新的立体有择合成。

  DOI：

  10.1016/s0040-4020(01)91575-3
• 作为产物：
  描述：

  1-戊炔 、 儿萘酚硼烷 反应 1.0h， 生成 (E)-pent-1-en-1-yl-1,3,2-benzodioxaborole
  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

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。
• Investigations into a Biomimetic Approach toward CP-225,917 and CP-263,114
  作者：Gary A. Sulikowski、Fabio Agnelli、R. Michael Corbett

  DOI：10.1021/jo9911286

  日期：2000.1.1

  A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C(16) anhydride derived from the condensation of lauric acid and oxaloacetic acid. An important element of this step is a templating effect imposed by two thioester linkages, reminiscent of a polyketide or fatty acid synthase pathway. On the basis of this principle,

  概述了结构复杂的非共轭CP-225,917（1）的生物合成。该提议中的关键步骤是由月桂酸和草酰乙酸缩合得到的C（16）酸酐的二聚化。此步骤的重要元素是两个硫酯键所产生的模板作用，让人联想到聚酮化合物或脂肪酸合酶途径。基于此原理，研究了以1，n-二醇系链为模板的两种C（11）酸酐的二聚化，导致了CP-225,917和CP-263,114的核心结构。
• A Rapid Entry to Natural and Unnatural Disubstituted Maleic Anhydrides
  作者：Robert M. Adlington、Jack E. Baldwin、Rhona J. Cox、Gareth J. Pritchard

  DOI：10.1055/s-2002-25344

  日期：——

  Copper-mediated tandem vicinal difunctionalisation of dimethyl acetylenedicarboxylate, followed in selected cases by oxidation of one of the substituents, provides a versatile and rapid route to a variety of natural and unnatural disubstituted maleic anhydrides.

  铜介导的乙炔二甲酸二甲酯的串联邻位双官能化反应，以及在某些情况下其中一个取代基的氧化反应，为获得各种天然和非天然的二取代马来酸酐提供了多用途的快速途径。
• 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.