3-methylhept-2(Z)-enal | 56161-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methylhept-2(Z)-enal
• 英文别名: (Z)-3-methyl-2-heptenal；(Z)-3-methyl-2-hepten-1-al；(Z)-3-methylhept-2-enal
• CAS: 56161-65-0
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: DVBAJGKNAHJKGX-VURMDHGXSA-N

物化性质

• 沸点：
  182.6±9.0 °C(Predicted)
• 密度：
  0.833±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methylhept-2(Z)-enal 在 四氯化钛 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 55.5h， 生成 (E)-6-[5-((Z)-3-Chloro-2,5-dimethyl-non-4-enoyl)-4-hydroxy-6-oxo-6H-pyran-2-yl]-hept-2-enoic acid methyl ester
  参考文献：
  名称：

  Myxopyronin B analogs as inhibitors of RNA polymerase, synthesis and biological evaluation

  摘要：

  A series of myxopyronin B analogs has been prepared via a convergent synthetic route and were tested for in vitro inhibitory activity against DNA-dependent RNA polymerase and antibacterial activity against E. coli and S. aureus. The parent lead compound proved to be very sensitive to even small changes. Only the achiral desmethyl myxopyronin B (1a) provided enhanced potency. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.045
• 作为产物：
  描述：

  1,1 dimethoxy 3-methyl 2(E)heptene 生成 3-methylhept-2(Z)-enal
  参考文献：
  名称：

  ALEXAKIS, A.;COMMERCON, A.;COULENTIANOS, C.;NORMANT, J. F., TETRAHEDRON, 1984, 40, N 4, 715-731

  摘要：

  DOI：

文献信息

• Lewis acid-catalyzed oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tet.2009.11.104

  日期：2010.1

  Two methods for the oxidative rearrangement of tertiary allylic alcohols have been developed. Most of tertiary allylic alcohols studied were oxidized to their corresponding transposed carbonyl derivatives in excellent to fair yields by reaction with TEMPO in combination with PhIO and Bi(OTf)3 or copper (II) chloride in the presence or not of oxygen. Other primary oxidants of TEMPO such as PhI(OAc)2

  已经开发了两种方法用于叔烯丙基醇的氧化重排。通过与TEMPO结合PhIO和Bi（OTf）3或氯化铜（II）在氧气存在或不存在的情况下反应，可以将所研究的大多数叔烯丙醇氧化成其相应的转座羰基衍生物，收率极好至合理。TEMPO的诸如岛（OAC）等初级氧化剂2，中号CPBA，过硫酸氢钾®不能令人满意给予烯酮在适度低的产率。
• Copper-Catalyzed Aerobic Oxidative Rearrangement of Tertiary Allylic Alcohols Mediated by TEMPO
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-0029-1217545

  日期：2009.8

  A mild method for the oxidative rearrangement of tertiary allylic alcohols to β-substituted enones using a TEMPO/CuCl 2 system, in the presence of molecular sieves, is described. Depending on the substrate, CuCl 2 was used in either a catalytic amount under an oxygen atmosphere or stoichiometrically.

  描述了在分子筛存在下使用 TEMPO/CuCl 2 系统将叔烯丙醇氧化重排为 β-取代烯酮的温和方法。取决于基材，CuCl 2 在氧气氛下以催化量或化学计量使用。
• Highly stereoselective synthesis of a sex pheromone of the dry bean beetleCallosobruchus analis
  作者：O. A. Pinsker、P. G. Tsiklauri、N. Ya. Grigor'eva

  DOI：10.1007/bf02495308

  日期：1999.7

  Total synthesis of 3-methylhept-2(Z)-enoic acid, a sex pheromone of the dry bean beetleCallosobruchus analis, has been performed using a previously developed highly stereoselective method of the construction of disubstituted (Z)-methylolefins based on the higher thermodynamic stability of (E)-isomers of α,β-disubstituted acroleins.

  3-methylhept-2(Z)-enoic acid 是干豆甲虫Callosobruchus analis 的一种性信息素，已使用先前开发的基于更高热力学的二取代（Z）-甲基烯烃构建的高度立体选择性方法进行了全合成α,β-二取代丙烯醛的 (E)-异构体的稳定性。
• Structure–Activity Relationship Study of Biselyngbyolide B Reveals Mitochondrial Fission-Induced Cytotoxicity in Cancer
  作者：Pratiti Mandal、Debobrata Paul、Himangshu Sharma、Sanu Saha、Partha Chakrabarti、Rajib Kumar Goswami

  DOI：10.1021/acsmedchemlett.4c00094

  日期：——

  A systematic structure–activity relationship study of the potent anticancer marine macrolide biselyngbyolide B has been accomplished. A total of 11 structural variants of the parent natural product, of which 2 are natural analogues, have been studied against a human colorectal carcinoma cell line. The requisite functional units of the parent molecule responsible for the cytotoxic activities have been

  已经完成了强效抗癌海洋大环内酯双色内酯 B 的系统构效关系研究。已经针对人结直肠癌细胞系研究了母体天然产物的总共 11 种结构变体，其中 2 种是天然类似物。负责细胞毒活性的母体分子必需的功能单元已被公开。 Biselyngbyolide C是biselyngbyolide B的天然类似物之一，人们对其分子机制进行了深入研究。有趣的是，体外数据表明，动力相关蛋白 1 介导的线粒体裂变和活性氧产生的诱导，导致结肠癌细胞中 ASK1/P38/JNK 介导的细胞凋亡的激活，这是双色内酯 B 介导的重要途径细胞毒性。值得注意的是，这项研究揭示了大环内酯参与线粒体裂变，促进癌细胞凋亡，提供了新的见解。
• Myxopyronin B analogs as inhibitors of RNA polymerase, synthesis and biological evaluation
  作者：Thomas Doundoulakis、Alan X. Xiang、Ricardo Lira、Konstantinos A. Agrios、Stephen E. Webber、Wes Sisson、Robert M. Aust、Amit M. Shah、Richard E. Showalter、James R. Appleman、Klaus B. Simonsen

  DOI：10.1016/j.bmcl.2004.08.045

  日期：2004.11

  A series of myxopyronin B analogs has been prepared via a convergent synthetic route and were tested for in vitro inhibitory activity against DNA-dependent RNA polymerase and antibacterial activity against E. coli and S. aureus. The parent lead compound proved to be very sensitive to even small changes. Only the achiral desmethyl myxopyronin B (1a) provided enhanced potency. (C) 2004 Elsevier Ltd. All rights reserved.