(1R,2R)-2-(乙酰氧基甲基)环丙烷羧酸 | 201337-81-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (1R,2R)-2-(乙酰氧基甲基)环丙烷羧酸
• 英文名称: (±)-trans-2-(acetoxymethyl)cyclopropanecarboxylic acid
• 英文别名: Cyclopropanecarboxylicacid, 2-[(acetyloxy)methyl]-, (1R,2R)-；(1R,2R)-2-(acetyloxymethyl)cyclopropane-1-carboxylic acid
• CAS: 201337-81-7
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: MORWYGLVZPSWQJ-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-(乙酰氧基甲基)环丙烷羧酸 在 咪唑 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 2,4,6-三氯苯甲酰氯 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 potassium tri-sec-butyl-borohydride 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 54.0h， 生成 (2S,4Z)-2-[(1R,2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
  参考文献：
  名称：

  Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone

  摘要：

  An efficient synthesis of a known precursor of halicholactone (1a) and neohalicholactone (1b) has been developed using the strategically functionalized key cyclopropane intermediate 2, which in turn has been synthesized via stereoselective cyclopropanation of trans-cinnamyl alcohol in the presence of the chiral dioxaborolane ligand 4. Elaboration of the above bifunctional cyclopropane to the target molecule was achieved in a relatively short reaction sequence and in good overall yield, representing a formal synthesis of the title compounds.

  DOI：

  10.1021/jo971564x
• 作为产物：
  描述：

  Acetic acid (1R,2R)-2-phenyl-cyclopropylmethyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 24.0h， 以93%的产率得到(1R,2R)-2-(乙酰氧基甲基)环丙烷羧酸
  参考文献：
  名称：

  Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone

  摘要：

  An efficient synthesis of a known precursor of halicholactone (1a) and neohalicholactone (1b) has been developed using the strategically functionalized key cyclopropane intermediate 2, which in turn has been synthesized via stereoselective cyclopropanation of trans-cinnamyl alcohol in the presence of the chiral dioxaborolane ligand 4. Elaboration of the above bifunctional cyclopropane to the target molecule was achieved in a relatively short reaction sequence and in good overall yield, representing a formal synthesis of the title compounds.

  DOI：

  10.1021/jo971564x

文献信息

• NAPHTHYRIDINES AS INHIBITORS OF HPK1
  申请人：Genentech, Inc.

  公开号：US20180282328A1

  公开（公告）日：2018-10-04

  Naphthyridine compounds and their use as inhibitors of HPK1 are described. The compounds are useful in treating HPK1-dependent disorders and enhancing an immune response. Also described are methods of inhibiting HPK1, methods of treating HPK1-dependent disorders, methods for enhancing an immune response, and methods for preparing the naphthyridine compounds.

  萘啶化合物及其作为HPK1抑制剂的用途被描述。这些化合物在治疗HPK1依赖性疾病和增强免疫反应方面很有用。还描述了抑制HPK1的方法、治疗HPK1依赖性疾病的方法、增强免疫反应的方法以及制备萘啶化合物的方法。
• ISOQUINOLINES AS INHIBITORS OF HPK1
  申请人：Genentech, Inc.

  公开号：US20180282282A1

  公开（公告）日：2018-10-04

  Isoquinoline compounds and their use as inhibitors of HPK1 (hematopoietic kinase 1) are described. The compounds are useful in treating HPK1-dependent disorders and enhancing an immune response. Also described are methods of inhibitng HPK1, methods of treating HPK1-dependent disorders, methods for enhancing an immune response, and methods for preparing the isoquinoline compounds.

  描述了异喹啉化合物及其作为HPK1（造血激酶1）抑制剂的用途。这些化合物在治疗依赖于HPK1的疾病和增强免疫应答方面非常有用。还描述了抑制HPK1的方法、治疗依赖于HPK1的疾病的方法、增强免疫应答的方法，以及制备异喹啉化合物的方法。
• Kinetic Enzymatic Resolution of Cyclopropane Derivatives
  作者：Jörg Pietruszka、Anja C. M. Rieche、Thorsten Wilhelm、Andreas Witt

  DOI：10.1002/adsc.200303137

  日期：2003.12

  enzymatic resolution of various cyclopropane derivatives was systematically investigated. The study focused on synthetically useful cyclopropylmethanols (e.g., 18a/j or 19a/j) as well as some rarely investigated cyclopropanols (e.g., 24/25 or 27). The combination of enantioselective catalytic or diastereoselective synthesis of enantiomerically enriched compounds with enzymatic approaches ultimately

  系统研究了各种环丙烷衍生物的动力学酶解。该研究集中于合成有用的环丙基甲醇（例如18a / j或19a / j）以及一些鲜有研究的环丙醇（例如24/25或27）。对映体富集化合物的对映选择性催化或非对映选择性合成与酶促方法的结合最终导致最方便的途径制备对映体纯的起始原料。再次证明了这一点，特别是对于环丙醇18a / j和19a / j的合成。成功进行研究的关键是严格建立一种分析工具，用于分析反应混合物的对映体组成。
• [EN] ISOQUINOLINES AS INHIBITORS OF HPK1<br/>[FR] ISOQUINOLÉINES UTILISÉES EN TANT QU'INHIBITEURS DE HPK1
  申请人：GENENTECH INC

  公开号：WO2018183964A1

  公开（公告）日：2018-10-04

  Isoquinoline compounds and their use as inhibitors of HPK1 (hematopoietic kinase 1) are described. The compounds are useful in treating HPK1 -dependent disorders and enhancing an immune response. Also described are methods of inhibiting HPK1, methods of treating HPK1 -dependent disorders, methods for enhancing an immune response, and methods for preparing the isoquinoline compounds.
• Stereoselective Synthesis of a Key Precursor of Halicholactone and Neohalicholactone
  作者：Debendra K. Mohapatra、Apurba Datta

  DOI：10.1021/jo971564x

  日期：1998.2.1

  An efficient synthesis of a known precursor of halicholactone (1a) and neohalicholactone (1b) has been developed using the strategically functionalized key cyclopropane intermediate 2, which in turn has been synthesized via stereoselective cyclopropanation of trans-cinnamyl alcohol in the presence of the chiral dioxaborolane ligand 4. Elaboration of the above bifunctional cyclopropane to the target molecule was achieved in a relatively short reaction sequence and in good overall yield, representing a formal synthesis of the title compounds.