2-chloro-5-methyl-hexa-1,5-diene | 116440-70-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-chloro-5-methyl-hexa-1,5-diene
• 英文别名: 2-Chloro-5-methylhexa-1,5-diene
• CAS: 116440-70-1
• 化学式: C₇H₁₁Cl
• 分子量: 130.617
• InChiKey: LTHUJBGUUIEHBS-UHFFFAOYSA-N

物化性质

• 沸点：
  134.4±19.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-chloro-5-methyl-hexa-1,5-diene 在 copper(l) iodide 、 2,5-二甲基-1,5-己二烯 、 甲基磺酰氯 、 三乙胺 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 生成 (4E)-4-(bromomethyl)-8-methylnona-1,4,8-triene
  参考文献：
  名称：

  Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization

  摘要：

  Tetraene 1 was prepared in nine steps from the known propargylic alcohol 7 in 17% overall yield or as a 2:1 E/Z mixture in only five steps in 7% overall yield. Oxidative cyclization of 1 with 2 equiv of Mn(OAc)(3). 2H(2)O and 1 equiv of Cu(OAc)(2) in MeOH at 25 degrees C provided 35% of tetracycle 2. Further elaboration provided (+/-)-isosteviol (3) in six steps in 51% yield and (+/-)-beyer-15-ene-3 beta,19-diol in four steps in 17% yield.

  DOI：

  10.1021/jo981238x
• 作为产物：
  描述：

  2,3-二氯丙烯 、 甲基烯丙基溴化镁 以77%的产率得到2-chloro-5-methyl-hexa-1,5-diene
  参考文献：
  名称：

  One-step construction of fused tricyclic and tetracyclic structures from acyclic precursors via cyclic carbopalladation

  摘要：

  DOI：

  10.1021/ja00179a058

文献信息

• Highly stereoselective synthesis of exocyclic alkenes via cyclialkylation
  作者：Ei-ichi Negishi、Yantao Zhang、Vahid Bagheri

  DOI：10.1016/s0040-4039(01)81055-8

  日期：1987.1

  Treatment of stereodefined ω-halo-2-iodoalkene derivatives (1), prepared via stereoselective addition reactions of alkynes, with either -BuLi (1 equiv) or -BuLi (2 equiv) can produce exocyclic alkenes whose isomeric purity is essentially 100%.

  通过炔烃的立体选择性加成反应与-BuLi（1当量）或-BuLi（2当量）制备的立体定义的ω-卤代-2-碘代烯烃衍生物（1）可以产生环外烯烃，其异构体纯度基本为100％。
• ZHANG, YANTAO;WU, GUANG-ZHONG;AGNEL, GILBERT;NEGISHI, EI-ICHI, J. AMER. CHEM. SOC., 112,(1990) N3, C. 8590-8592
  作者：ZHANG, YANTAO、WU, GUANG-ZHONG、AGNEL, GILBERT、NEGISHI, EI-ICHI

  DOI：——

  日期：——
• NEGISHI, EI-ICHI;ZHANG, YANTAO;BAGHERI, VAHID, TETRAHEDRON LETT., 28,(1987) N 47, 5793-5796
  作者：NEGISHI, EI-ICHI、ZHANG, YANTAO、BAGHERI, VAHID

  DOI：——

  日期：——
• Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization
  作者：Barry B. Snider、Jane Y. Kiselgof、Bruce M. Foxman

  DOI：10.1021/jo981238x

  日期：1998.10.1

  Tetraene 1 was prepared in nine steps from the known propargylic alcohol 7 in 17% overall yield or as a 2:1 E/Z mixture in only five steps in 7% overall yield. Oxidative cyclization of 1 with 2 equiv of Mn(OAc)(3). 2H(2)O and 1 equiv of Cu(OAc)(2) in MeOH at 25 degrees C provided 35% of tetracycle 2. Further elaboration provided (+/-)-isosteviol (3) in six steps in 51% yield and (+/-)-beyer-15-ene-3 beta,19-diol in four steps in 17% yield.
• One-step construction of fused tricyclic and tetracyclic structures from acyclic precursors via cyclic carbopalladation
  作者：Yantao Zhang、Guang Zhong Wu、Gilbert Agnel、Ei Ichi Negishi

  DOI：10.1021/ja00179a058

  日期：1990.11