2,2-dichloro-3-methyl-3-vinyl-1-cyclobutanone | 82873-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dichloro-3-methyl-3-vinyl-1-cyclobutanone
• 英文别名: 2,2-Dichloro-3-methyl-3-vinylcyclobutanone；2,2-Dichloro-3-ethenyl-3-methylcyclobutan-1-one
• CAS: 82873-91-4
• 化学式: C₇H₈Cl₂O
• 分子量: 179.046
• InChiKey: RKWVHFKZRXJLIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2,2-dichloro-3-methyl-3-vinyl-1-cyclobutanone 生成 3-methyl-3-vinyl-1-cyclobutanone
  参考文献：
  名称：

  MORI, KENJI;UEMATSU, TAMON

  摘要：

  DOI：
• 作为产物：
  描述：

  三氯乙酰氯 、 天然橡胶 在 三氯氧磷 作用下， 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 为溶剂， 以86.5%的产率得到2,2-dichloro-3-methyl-3-vinyl-1-cyclobutanone
  参考文献：
  名称：

  Production method of an insect pheromone

  摘要：

  一种生产用于昆虫信息素的3,3,7-三甲基-2,9-二氧杂三环[3.3.1.0.sup.4,7]壬烷的方法，其化学式为 ##STR1## 包括用二异丁基铝氢化物还原1,5,5-三甲基-7-内-叔丁基二甲基硅氧基-4-氧杂双环[4.2.0]辛烷-3-酮，并在去除硅保护基后用酸处理。

  公开号：

  US04511726A1

文献信息

• Synthesis and absolute configuration of both the enantiomers of lineatin
  作者：Kenji Mori、Tamon Uematsu、Masao Minobe、Kazunori Yanagi

  DOI：10.1016/s0040-4020(01)88680-4

  日期：1983.1

  A new synthesis of (±)-, (+)- and ( − )- lineatin (3,3,7 - trimethyl - 2,9 - dioxatricyclo[3.3.1.04,7]nonane) 1 was achieved. The stereochemistry of ( + )-lineatin was established as (1R, 4S, 5R, 7R) by an X-ray crystallographic analysis of an intermediate 15.

  实现了（±）-，（+）-和（-）-可乐宁（3,3,7-三甲基-2,9-二氧三环[3.3.1.0 4,7 ]壬烷）1的新合成。通过中间体15的X射线晶体学分析，确定（+）-lineatin的立体化学为（1R，4S，5R，7R）。
• Preparation and Photosensitized Oxidation of Isopropylidenecyclobutanes and -cyclobutenes
  作者：Aryeh A. Frimer、Joseph Weiss、Hugo E. Gottlieb、Joel L. Wolk

  DOI：10.1021/jo00083a019

  日期：1994.2

  Isopropylidenecyclobutanes 2-5 underwent facile ene reaction with singlet dioxygen, yielding (upon Ph(3)P reduction) the corresponding pairs of epimeric allylic alcohols 9 and 10, 11 and 12, 13 and 14, and 15 and 16, respectively. A combination of spectral evidence and molecular modeling studies were utilized in the structural assignment of the epimers. The data clearly indicate that steric considerations play an important role in determining the face of the ring which O-1(2) approaches. Isopropylidenecyclobutenes 6 and 7 reacted with singlet oxygen more slowly than their monoolefinic analogs, yielding upon reduction allylic alcohols 21b and 22, respectively. Benzo analog 7 also generated a small and solvent-dependent amount of isomeric aldehydes 23 and 24, presumably via a free-radical mechanism. n-Butyl diene 8 underwent rapid photosensitized oxygenation producing allylic alcohol 35 (as the O-1(2) ene product) and dione 37 (the Hock-cleavage product of allylic hydroperoxide 39, formed in turn via a free-radical route) in a 1:9 ratio. Ah initio (STO-3G) calculations confirm that, in their lowest energy conformations, compounds 2-8 are planar with the methylene ring hydrogens displaced ca. 36 degrees from the perpendicular. As a result, only exocyclic ene product is formed, since O-1(2) strongly prefers axial or pseudoaxial allylic hydrogens. These calculations combined with the relative rate data suggest that the initial interaction between the electrophilic O-1(2) and alkylidenecyclobutenes involves both ends of the singlet dioxygen molecule, in which the ''front'' end attacks the reactive exocyclic double bond while the ''back'' end obtains stabilization by interacting with the more electron rich but unreactive endocyclic olefin linkage. Because of this added, and presumably substantial, stabilization, the relative rates within this system are determined in part by the orbital coefficients at the latter olefinic center.
• Synthesis and absolute configuration of +-lineatin, the pheromone of
  作者：Kenji Mori、Tamon Uematsu、Masao Minobe、Kazunori Yanagi

  DOI：10.1016/s0040-4039(00)87222-6

  日期：1982.1
• MORI, KEHJDZI;UEHMATSU, TAKAN
  作者：MORI, KEHJDZI、UEHMATSU, TAKAN

  DOI：——

  日期：——
• JPS58110534A
  申请人：——

  公开号：JPS58110534A

  公开（公告）日：1983-07-01