(Z)-3-methylhept-2-en-1-ol | 22882-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-3-methylhept-2-en-1-ol
• 英文别名: 3-Methyl-(Z)-2-hepten-1-ol；3-methylhept-2(Z)-en-1-ol；(Z)-3-Methyl-2-heptenol；(Z)-3-methyl-hept-2-en-1-ol
• CAS: 22882-85-5
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: IIFRHZRUHAELRO-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-methylhept-2-en-1-ol 生成 cis-3-Methyl-2-heptenylpyrophosphat
  参考文献：
  名称：

  3-甲基-2-烯基焦磷酸盐与异戊烯基焦磷酸盐的酶促缩合。

  摘要：

  DOI：

  10.1021/ja00723a037
• 作为产物：
  描述：

  1-benzyloxy-3-methylhept-2(Z)-ene 在 lithium 作用下， 以 氨 为溶剂， 反应 2.5h， 以81%的产率得到(Z)-3-methylhept-2-en-1-ol
  参考文献：
  名称：

  干豆甲虫Callosobruchus analis的性信息素的高度立体选择性合成

  摘要：

  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。

  DOI：

  10.1007/bf02495308

文献信息

• Rhenium-Catalyzed 1,3-Isomerization of Allylic Alcohols: Scope and Chirality Transfer
  作者：Christie Morrill、Gregory L. Beutner、Robert H. Grubbs

  DOI：10.1021/jo061436l

  日期：2006.9.1

  The scope of the triphenylsilyl perrhennate (O3ReOSiPh3, 1) catalyzed 1,3-isomerization of allylic alcohols has been thoroughly explored. It was found to be effective for a wide variety of secondary and tertiary allylic alcohol substrates bearing aryl, alkyl, and cyano substituents. Two general reaction types were found which gave high levels of product selectivity: those driven by formation of an

  的三苯基perrhennate的（范围ø 3 ReOSiPh 3，1）催化的烯丙基醇的1,3-异构化已得到彻底探索。已发现对于具有芳基，烷基和氰基取代基的多种仲和叔烯丙基醇底物是有效的。发现了两种提供高水平产物选择性的常规反应类型：那些是通过形成扩展的共轭体系驱动的，以及是由特定异构体的选择性甲硅烷基化驱动的。研究了在各种底物上的手性转移效率，并发现了可以形成高对映选择性的仲和叔烯丙基醇的条件。考虑到围绕烯丙基系统周围的取代基的性质的选择性趋势表明，这是用于烯丙基醇合成的可靠且可预测的方法。
• Pheromone study on acarid mites. Part IX. Syntheses of alarm pheromone analogues of the mold mite, Tyrophagus putrescentiae, and their biological activities.
  作者：Yasumasa KUWAHARA、Lica SAKUMA

  DOI：10.1271/bbb1961.46.1855

  日期：——

  Against the mold mite, Tyrophagus putrescentiae, 3, 7-dimethyl-(Z)-2-octenyl formate (II) is the most active compound as an alarm pheromone besides the natural pheromone, neryl formate (I), and this activity is equal to I (1-10ppm). In order to elucidate the structural requisites for inducing alarm pheromone activity, a total of 16 analogues of I were prepared by modifying the structure of II. For preparation of 3-methyl- and 3-ethyl-(Z)-2-alkenyl formates, the Wittig reaction of ethoxy- or methoxy-carbonylmethylene triphenyl phosphorane with 2-alkanone or 3-alkanone was used. The reaction with 2-alkanone gave a mixture of (Z)-2-alkenoate (ca. 40%) and (E)-2-alkenoate (ca. 60%) in an average 60% yield. The reaction with 3-alkanone gave a mixture of (Z)-2-alkenoate (56%) and (E)-2-alkenonate (44%). Alarm pheromone activities were demonstrated on 14 compounds of (Z)-2-alkenyl formates. The presence of the (Z)-allylic primary alcohol formate moiety in a molecule was clarified as the key to induce pheromone activity, and no necessity for an acyclic monoterpene carbon skeleton was demonstrated.

  针对霉菌螨（Tyrophagus putrescentiae），3, 7-二甲基-(Z)-2-辛烯酸甲酯（II）是除了天然信息素（奈尔酸甲酯 I）外，作为警报信息素最活跃的化合物，其活性与 I 相当（1-10ppm）。为了阐明诱导警报信息素活性的结构要求，制备了16个 I 的类似物，通过改造 II 的结构。为制备3-甲基和3-乙基-(Z)-2-烯酸甲酯，采用了乙氧基或甲氧基碳酰基甲烯三苯基膦与2-烷酮或3-烷酮的威蒂格反应。与2-烷酮的反应产生了约40%的(Z)-2-烯酸酯和约60%的(E)-2-烯酸酯，平均产率为60%。与3-烷酮的反应则得到了56%的(Z)-2-烯酸酯和44%的(E)-2-烯酸酯。在14种(Z)-2-烯酸甲酯化合物中展示了警报信息素活性。研究表明，分子中存在(Z)-烯丙基初级醇酸甲酯基团是诱导信息素活性的关键，且不需要非环状单萜碳骨架。
• Specific hydromagnesiation of prop-2-ynylic alcohols. A simple and specific route to terpenoids
  作者：Fumie Sato、Hiroaki Ishikawa、Hiroshi Watanabe、Tooru Miyake、Masao Sato

  DOI：10.1039/c39810000718

  日期：——

  Hydromagnesiation of prop-2-ynylic alcohols proceeds with stereo- and regio-specificity, affording, under mild conditions, the alkenylmagnesium halides (5) in almost quantitative yields, thus providing a novel and simple route to terpenoids.

  丙-2-炔醇的加氢镁化具有立体和区域特异性，在温和条件下以几乎定量的产率提供链烯基卤化镁（5），从而提供了一种新颖且简单的制备萜类化合物的途径。
• 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。
• Chromium(II)-Mediated Stereodivergent Additions of Allylic Phosphates and Halides to Aldehydes
  作者：Stefan Nowotny、Charles E. Tucker、Carole Jubert、Paul Knochel

  DOI：10.1021/jo00114a026

  日期：1995.5

  The addition of gamma-disubstituted allylchromium(III) reagents to aldehydes proceeds in a stereodivergent manner, in contrast to the case of gamma-monosubstituted allylchromium(III) species. The method allows the preparation of a variety of homoallylic alcohols bearing a quaternary center of defined relative configuration in the alpha-position. The preparation of both stereomeric homoallylic alcohols 13 is possible by using either of the two (E)- or (Z)-allylic precursors. The reaction has been extended to a gamma-monosubstituted beta-(trimethylsilyl)allylic system. The intermediate allylic chromium(III) reagents can be conveniently prepared from the corresponding phosphates (or chlorides) in DMPU or THF in the presence of catalytic amounts of LiI.