cis-3,4-epoxy-6-phenyl-1-hexene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-3,4-epoxy-6-phenyl-1-hexene
• 英文别名: cis-1-phenyl-3,4-epoxyhex-5-ene；(2R,3S)-2-ethenyl-3-(2-phenylethyl)oxirane
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: LCKQHBKRSNYMRU-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-3,4-epoxy-6-phenyl-1-hexene 在 三(五氟苯基)硼烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到(1S*,2R*)-1-vinyl-1,2,3,4-tetrahydronaphthalen-2-ol
  参考文献：
  名称：

  路易斯酸催化的乙烯基环氧乙烷的立体选择性碳环化：Musellarin三环核心的构建

  摘要：

  乙烯基氧杂环丁烷的立体选择性碳环化被路易斯酸有效地催化，以提供环状均烯丙基醇作为单一异构体。在顺式乙烯基环氧乙烷的情况下，路易斯酸B（C 6 F 5）3的选择对于立体选择性转化至关重要，而事实证明BF 3 ∙OEt 2是反式底物的有效催化剂。该方法在具有官能团耐受性的七元环和六元环的合成中得到了很好的实现。所得的效用反式-和顺高烯丙基醇被证明简明地建立musellarin A和E的三环核心

  DOI：

  10.1002/bkcs.12236
• 作为产物：
  描述：

  10-[2-[(3R,4S)-4-hydroxy-6-phenylhex-1-en-3-yl]oxybenzimidazol-1-yl]decane-2,5,8-trione 以78%的产率得到
  参考文献：
  名称：

  YAMAGUCHI, MASAHIKO;MUKAIYAMA, TERUAKI, CHEM. LETT, 1982, N 2, 237-240

  摘要：

  DOI：

文献信息

• A simple, stereoselective, room-temperature synthesis of cis vinyloxiranes and trans 1-phenyl-1,3-butadiene
  作者：Jacques Auge、Serge David

  DOI：10.1016/s0040-4039(00)88249-0

  日期：1983.1

  The organotin reagent from 1-chloro-3-iodoprop-1-ene and SnCl2 in dimethylformamide reacted with aldehydes by ite chlorine-substituted carbon atom. Treatment with NaOMe then gave vinyloxiranes with good stereo-selectivity. benzaldehyde and 1-bromo-3-iodoprop-1-ene in the presence of two equivalents of SnCl2 gave exclusively -1-phenyl-1,3-butadiene.

  1-氯-3-碘丙-1-烯和SnCl 2在二甲基甲酰胺中的有机锡试剂通过氯取代的碳原子与醛反应。然后用NaOMe处理得到具有良好立体选择性的乙烯基环氧乙烷。在两当量的SnCl 2存在下，苯甲醛和1-溴-3-碘丙-1-烯仅产生-1-苯基-1,3-丁二烯。
• THE HIGHLY STEREOSELECTIVE SYNTHESIS OF<i>CIS</i>-VINYLOXIRANES
  作者：Masahiko Yamaguchi、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.237

  日期：1982.2.5

  In the presence of triethylaluminum, oxyallyl anions derived from 2-allyloxybenzimidazoles react with aldehydes in highly regio-and stereoselective manner to afford α-adducts in good yields. The adducts are stereospecifically converted to cis-vinyloxiranes in good yields.

  在三乙基铝的存在下，源自2-烯丙氧基苯并咪唑的氧烯丙基阴离子与醛类反应，呈现出高度的区位选择性和立体选择性，获得良产率的α-加成物。这些加成物以立体专一的方式转化为良产率的顺式烯丙基亚氧化物。
• Formation of cyclopropyl carbinols through a highly diastereoselective hydrozirconation of vinyloxirane derivatives
  作者：Susumu Harada、Noboru Kowase、Takeo Taguchi、Yuji Hanzawa

  DOI：10.1016/s0040-4039(97)00233-5

  日期：1997.3

  Cyclopropyl carbinol derivatives were efficiently prepared through a highly diastereoselective hydrozirconation of vinyloxirones and the intramolecular nucleophilic attack of the generated alkylzirconocene with the inversion of the configuration at the reacting oxirane carbon.

  环丙基甲醇衍生物可通过乙烯基氧杂环丁烷的高度非对映选择性加氢锆化反应以及生成的烷基锆茂茂的分子内亲核攻击以及在环氧乙烷碳原子上构型的反转而有效地制备。
• Julia, Marc; Verpeaux, Jean-Noel; Zahneisen, Thomas, Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 539 - 554
  作者：Julia, Marc、Verpeaux, Jean-Noel、Zahneisen, Thomas

  DOI：——

  日期：——
• Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols
  作者：Susumu Harada、Noboru Kowase、Nobuhito Tabuchi、Takeo Taguchi、Yasuo Dobashi、Akira Dobashi、Yuji Hanzawa

  DOI：10.1016/s0040-4020(97)10340-4

  日期：1998.1

  Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1-butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl. (C) 1997 Elsevier Science Ltd. All rights reserved.