2-(hydroxymethyl)hexanoic acid | 58243-89-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(hydroxymethyl)hexanoic acid
• CAS: 58243-89-3
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: ICBHDGOFKNWYJO-UHFFFAOYSA-N

物化性质

• 沸点：
  273.6±23.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)hexanoic acid 在 吡啶 、 锂硼氢 、 R(+)-alpha-甲基苄胺 、 四丁基溴化铵 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 生成 (2R)-2-({[(phenylmethyl)oxy]amino}methyl)hexanoic acid
  参考文献：
  名称：

  Synthesis and in vitro antibacterial activity of oxazolidine LBM-415 analogs as peptide deformylase inhibitors

  摘要：

  The drug resistant bacteria pose a severe threat to human health. The increasing resistance of those pathogens to traditional antibacterial therapy renders the identification of new antibacterial agents with novel antibacterial mechanisms an urgent need. In this study, a series of (2S)-N-substituted-1-[(formyhydroxyamino) methyl]-1-oxohexyl]-2-oxazolidinecarboxamides were designed, synthesized and evaluated for in vitro antibacterial activity. Most of these compounds displayed good activities against Gram-positive organisms comparable to reference agent LBM-415. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.097
• 作为产物：
  描述：

  butylmalonic acid monoethyl ester 在 锂硼氢 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 4.5h， 生成 2-(hydroxymethyl)hexanoic acid
  参考文献：
  名称：

  （R）-2-丁基-3-羟基丙酸的高效合成

  摘要：

  描述了通过（±）-2-丁基-3-羟基丙酸（7）与（R）-α-甲基苄基胺的经典拆分有效合成（R）-2-丁基-3-羟基丙酸（1）的方法。（±）-2-丁基-3-羟基丙酸（7）可容易地从丙二酸二丁酯（2）中分两步获得。还描述了用猪肝酯酶和α-胰凝乳蛋白酶对1进行2的对映选择性酶水解的结果。

  DOI：

  10.1021/op060199l

文献信息

• NOVEL PROCESSES FOR THE PREPARATION OF PHENYLCYCLOPROPYLAMINE DERIVATIVES AND USE THEREOF FOR PREPARING TICAGRELOR
  申请人：Khile Anil Shahaji

  公开号：US20130165696A1

  公开（公告）日：2013-06-27

  Provided herein are novel processes for the preparation of phenylcyclopropylamine derivatives, which are useful intermediates in the preparation of triazolo[4,5-d]pyrimidine compounds. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of a substantially pure ticagrelor intermediate, trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine. Provided further herein are novel acid addition salts of trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine, and process for their preparation. The intermediate and its acid addition salts are useful for preparing ticagrelor, or a pharmaceutically acceptable salt thereof, in high yield and purity.

  本文提供了一种制备苯基环丙胺衍生物的新型工艺，这些衍生物在三唑并[4,5-d]嘧啶化合物的制备中是有用的中间体。特别提供了一种新颖、商业可行且在工业上具有优势的工艺，用于制备一种基本纯的替卡格雷中间体，即trans-(1R,2S)-2-(3,4-二氟苯基)-环丙胺。此外，本文还提供了trans-(1R,2S)-2-(3,4-二氟苯基)-环丙胺的新型酸加盐，以及其制备工艺。该中间体及其酸加盐对于高产率和纯度制备替卡格雷或其药用可接受盐是有用的。
• Ligand-Enabled Monoselective β-C(sp³)–H Acyloxylation of Free Carboxylic Acids Using a Practical Oxidant
  作者：Zhe Zhuang、Alastair N. Herron、Zhoulong Fan、Jin-Quan Yu

  DOI：10.1021/jacs.0c01214

  日期：2020.4.8

  recent disclosure of the β-lactonization of free aliphatic acids, the use of peroxides in C-H activation reactions directed by weakly coordinating native functional groups was unreported. Herein we report C(sp3)-H β-acetoxylation and γ-, δ-, and ε-lactonization reactions of free carboxylic acids enabled by a novel cyclopentane-based mono-N-protected β-amino acid (MPAA) ligand. Notably, tert-butyl hydrogen

  开发使用廉价且实用的氧化剂的 CH 活化反应仍然是一个重大挑战。在我们最近公开游离脂肪酸的 β-内酯化之前，过氧化物在由弱配位天然官能团指导的 CH 活化反应中的使用还没有报道。在此，我们报告了由新型环戊烷基单-N-保护的 β-氨基酸 (MPAA) 配体实现的游离羧酸的 C(sp3)-H β-乙酰氧基化和 γ-、δ- 和 ε-内酯化反应。值得注意的是，叔丁基过氧化氢 (TBHP) 被用作这些反应的唯一氧化剂。与其他 CH 活化方案相比，该反应具有几个关键优势：(1) 在存在两个 α-甲基基团的情况下观察到唯一的单选择性；(2) 含有α-氢的脂肪族羧酸与本协议兼容；
• NOVEL PROCESS FOR PREPARING PHENYLCYCLOPROPYLAMINE DERIVATIVES USING NOVEL INTERMEDIATES
  申请人：Khile Anil Shahaji

  公开号：US20130150577A1

  公开（公告）日：2013-06-13

  Provided herein is a novel process for the preparation of phenylcyclopropylamine derivatives, which are useful intermediates in the preparation of triazolo[4,5-d]pyrimidine compounds. Provided particularly herein is a novel, commercially viable and industrially advantageous process for the preparation of a substantially pure ticagrelor intermediate, trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine. The intermediate is useful for preparing ticagrelor, or a pharmaceutically acceptable salt thereof, in high yield and purity.

  本文提供了一种新颖的制备苯基环丙胺衍生物的过程，这些衍生物在三唑并[4,5-d]嘧啶化合物的制备中是有用的中间体。特别提供了一种新颖的、商业可行且在工业上具有优势的过程，用于制备一种基本纯净的替卡格雷中间体，即trans-(1R,2S)-2-(3,4-二氟苯基)-环丙胺。该中间体可用于高产率和纯度地制备替卡格雷或其药学上可接受的盐。
• Catalytic Hydrogenation of Cyclic Carbonates: A Practical Approach from CO₂and Epoxides to Methanol and Diols
  作者：Zhaobin Han、Liangce Rong、Jiang Wu、Lei Zhang、Zheng Wang、Kuiling Ding

  DOI：10.1002/anie.201207781

  日期：2012.12.21

  Two birds with one stone: The simultaneous production of two important bulk chemicals, methanol and ethylene glycol, from CO2 and ethylene oxide has been achieved under mild conditions by the highly efficient homogeneous catalytic hydrogenation of ethylene carbonate in the presence of a (PNP)RuII catalyst (see scheme).

  两只鸟只有一块石头：在（PNP）的存在下，碳酸亚乙酯的高效均相催化加氢反应在温和的条件下实现了从CO 2和环氧乙烷同时生产两种重要的散装化学品甲醇和乙二醇钌II催化剂（参见方案）。
• [EN] PROCESS FOR PREPARING INTERMEDIATES<br/>[FR] PROCEDE DE PREPARATION D'INTERMEDIAIRES
  申请人：NOVARTIS AG

  公开号：WO2004026824A1

  公开（公告）日：2004-04-01

  The present invention is directed to a process for preparing intermediates that are useful to prepare certain antibacterial N-formyl hydroxylamine compounds which are peptide deformylase inhibitors. The process makes use α β-lactam intermediate. Certain optically pure intermediates are also claimed.

  本发明涉及一种用于制备中间体的方法，这些中间体对制备某些抗菌N-甲酰羟胺化合物（肽变形酶抑制剂）很有用。该方法利用αβ-内酰胺中间体。还要求某些光学纯中间体。