β-(n-pentyl)methacryloyl chloride | 303142-78-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: β-(n-pentyl)methacryloyl chloride
• 英文别名: (E)-2-methyloct-2-enoyl chloride
• CAS: 303142-78-1
• 化学式: C₉H₁₅ClO
• 分子量: 174.671
• InChiKey: IAJXDZINIPJIDU-BQYQJAHWSA-N

物化性质

• 沸点：
  226.0±9.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  β-(n-pentyl)methacryloyl chloride 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 (E,2S)-2-methyl-2-(phenylmethoxymethyl)oct-3-enal
  参考文献：
  名称：

  Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines

  摘要：

  Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00937-0
• 作为产物：
  描述：

  (E)-2-methyloct-2-enoic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.0h， 以93%的产率得到β-(n-pentyl)methacryloyl chloride
  参考文献：
  名称：

  Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines

  摘要：

  Enantioselective synthesis of the cyclopentenedione moiety of madindolines was achieved. Stereoselective construction of a quaternary carbon was realized by alkylation of an enolate possessing chiral auxiliary. Cyclopentenedione was derived from a triketone precursor by intramolecular condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00937-0

文献信息

• A new steroselective route to .GAMMA.-butyrolactones: asymmetric syntheses of (+)-trans-whisky and (+)-trans-cognac lactones.
  作者：Okiko MIYATA、Tetsuro SHINADA、Nanako KAWAKAMI、Kyoko TAJI、Ichiya NINOMIYA、Takeaki NAITO、Tadamasa DATE、Kimio OKAMURA

  DOI：10.1248/cpb.40.2579

  日期：——

  A new stereoselective route to γ-butyrolactones such as (+)-trans-whisky and (+)-trans-cognac lactones (1a, b) has been developed by a combination of three key reactions : diastereoselective nucleophilic addition of thiophenol, cleavage of chiral N-acylsultam via thioester, and intramolecular displacement of the sulfonium group with carboxylate anion.

  通过结合三个关键反应：噻吩酚的非对映选择性亲核加成、手性 N-acylsultam 通过硫酯的裂解以及羧酸阴离子对锍基团的分子内置换，我们开发出了一条新的立体选择性路线来制备γ-丁内酯，如 (+)-trans-whisky 和 (+)-trans-cognac 内酯 (1a，b)。