2-Methylcyclopropanol | 62808-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methylcyclopropanol
• 英文别名: 2-Methylcyclopropan-1-ol
• CAS: 62808-70-2
• 化学式: C₄H₈O
• 分子量: 72.1069
• InChiKey: IWOYJFLNKCFMOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-Methylcyclopropanol 、 苯甲酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Enantioselective Homocrotylboration of Aliphatic Aldehydes

  摘要：

  A practical route to optically pure syn-homocrotylation reagents is described, including highly diastereo- and enantioselective preparation of numerous syn-homocrotyl products, as well as several matched mismatched pairs. NMR experiments suggest that the active homocrotylating species is a cyclopropylcarbinyldichloroborane generated by chloride exchange from the PhBCl2 activator. Computational studies support the intermediacy of chloroboranes and suggest that homoallyl/homocrotyl transfers occur through Zimmerman-Traxler transition states.

  DOI：

  10.1021/ja311061n
• 作为产物：
  描述：

  4,4,5,5-tetramethyl-2-(2-methylcyclopropyl)-1,3,2-dioxaborolane 在 sodium peroxoborate tetrahydrate 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 生成 2-Methylcyclopropanol
  参考文献：
  名称：

  Enantioselective syn and anti Homocrotylation of Aldehydes: Application to the Formal Synthesis of Spongidepsin

  摘要：

  Whereas crotylboration has been a useful method for synthesis of stereochemically complex products, we have shown that homocrotylboration can be achieved with cyclopropanated crotylation reagents, and that the stereo-selectivity of the reaction can be predicted by analogous models. This paper presents a full account of this work, including the first examples of asymmetric anti homocrotylation. The scope of this reaction is demonstrated with highly enantioselective homocrotylation of both aliphatic and aromatic aldehydes, as well as double diastereoselection studies. An application of the synthesis of the marine natural product spongidepsin is presented, as well as streamlined syntheses of homocrotylation reagents.

  DOI：

  10.1021/jacs.5b08858

文献信息

• [EN] MTA-COOPERATIVE PRMT5 INHIBITORS<br/>[FR] INHIBITEURS DE PRMT5 COOPÉRATIF À BASE DE MTA
  申请人：MIRATI THERAPEUTICS INC

  公开号：WO2022192745A1

  公开（公告）日：2022-09-15

  Disclosed are compounds of Formula IIA, IIA-1, IIB, IIB-1, IIC and IIC-1: and pharmaceutical compositions and methods of use thereof These compounds inhibit Protein Arginine M-Methyl Transferase 5 (PRMT5) activity and are useful in methods and pharmaceutical compositions for treating cancer.

  本发明涉及化合物IIA、IIA-1、IIB、IIB-1、IIC和IIC-1，以及它们的药物组成物和使用方法。这些化合物抑制蛋白质精氨酸甲基转移酶5（PRMT5）的活性，并可用于治疗癌症的方法和药物组成物。
• Enantioselective Homocrotylboration of Aliphatic Aldehydes
  作者：Hongkun Lin、Wenbo Pei、Hao Wang、Kendall N. Houk、Isaac J. Krauss

  DOI：10.1021/ja311061n

  日期：2013.1.9

  A practical route to optically pure syn-homocrotylation reagents is described, including highly diastereo- and enantioselective preparation of numerous syn-homocrotyl products, as well as several matched mismatched pairs. NMR experiments suggest that the active homocrotylating species is a cyclopropylcarbinyldichloroborane generated by chloride exchange from the PhBCl2 activator. Computational studies support the intermediacy of chloroboranes and suggest that homoallyl/homocrotyl transfers occur through Zimmerman-Traxler transition states.
• WO2023/158708
  申请人：——

  公开号：——

  公开（公告）日：——
• Enantioselective <i>syn</i> and <i>anti</i> Homocrotylation of Aldehydes: Application to the Formal Synthesis of Spongidepsin
  作者：Hongkun Lin、Leiming Tian、Isaac J. Krauss

  DOI：10.1021/jacs.5b08858

  日期：2015.10.14

  Whereas crotylboration has been a useful method for synthesis of stereochemically complex products, we have shown that homocrotylboration can be achieved with cyclopropanated crotylation reagents, and that the stereo-selectivity of the reaction can be predicted by analogous models. This paper presents a full account of this work, including the first examples of asymmetric anti homocrotylation. The scope of this reaction is demonstrated with highly enantioselective homocrotylation of both aliphatic and aromatic aldehydes, as well as double diastereoselection studies. An application of the synthesis of the marine natural product spongidepsin is presented, as well as streamlined syntheses of homocrotylation reagents.