2,3-O-isopropylidene-L-tartaric acid dichloride | 443287-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-L-tartaric acid dichloride
• 英文别名: (S,S)-2,3-O-isopropylidene tartaric acid dichloride；D-2,3-O-isopropylidenetartaric dichloride
• CAS: 443287-71-6
• 化学式: C₇H₈Cl₂O₄
• 分子量: 227.044
• InChiKey: GGNFPJCUROZKLT-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-L-tartaric acid dichloride 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 (4S,5S)-4,5-bis(benzoxazol-2-yl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of novel C2-symmetric and enantiomerically pure bisbenzoxazoles and bisbenzothiazoles derived from l- and d-tartaric acids

  摘要：

  Five pairs of novel G-symmetric and enantiomerically pure bisbenzoxazoles and a pair of bisbenzothiazoles derived from L- and D-tartaric acids have been synthesized from L- and D-2,3-O-isopropylidenetartaric dichlorides and o-aminophenol derivatives or o-amino thio phenol, respectively, in two- or one-step reactions. The mechanism for the formation of bisbenzoxazoles and bisbenzothiazoles was suggested. The UV and H-1 NMR spectra showed that no coordination between the bisbenzoheterazoles and Cu(I) or Ni(II) cations occurred due to the lack of a sufficiently basic nitrogen donor atom in the benzoheterazole moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00547-x
• 作为产物：
  描述：

  (4S,5S)-2,2-二甲基-1,3-二恶茂-4,5-二甲酸二乙酯 在 lithium hydroxide 、 草酰氯 、 18-冠醚-6 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 水 为溶剂， 生成 2,3-O-isopropylidene-L-tartaric acid dichloride
  参考文献：
  名称：

  Synthesis of novel C2-symmetric and enantiomerically pure bisbenzoxazoles and bisbenzothiazoles derived from l- and d-tartaric acids

  摘要：

  Five pairs of novel G-symmetric and enantiomerically pure bisbenzoxazoles and a pair of bisbenzothiazoles derived from L- and D-tartaric acids have been synthesized from L- and D-2,3-O-isopropylidenetartaric dichlorides and o-aminophenol derivatives or o-amino thio phenol, respectively, in two- or one-step reactions. The mechanism for the formation of bisbenzoxazoles and bisbenzothiazoles was suggested. The UV and H-1 NMR spectra showed that no coordination between the bisbenzoheterazoles and Cu(I) or Ni(II) cations occurred due to the lack of a sufficiently basic nitrogen donor atom in the benzoheterazole moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00547-x

文献信息

• A Chiral Pool Strategy for the Synthesis of Enantiopure Hydroxymethyl-Substituted Pyridine Derivatives
  作者：Christian Eidamshaus、Hans-Ulrich Reissig

  DOI：10.1002/ejoc.201100681

  日期：2011.10

  A simple procedure for the synthesis of enantiopure hydroxymethyl-substituted pyridine derivatives is presented. The developed method is based on TMSOTf-promoted cyclocondensations of β-ketoenamides, leading to differently substituted 4-hydroxypyridine/4-pyridone derivatives. The required β-ketoenamides were prepared by acylation ofeasily available enamino ketones with suitably protected enantiopure

  介绍了合成对映体纯羟甲基取代吡啶衍生物的简单程序。开发的方法基于 TMSOTf 促进的 β-酮烯酰胺环缩合反应，导致不同取代的 4-羟基吡啶/4-吡啶酮衍生物。所需的 β-酮烯酰胺是通过将容易获得的烯氨基酮与适当保护的对映体纯羧酰氯酰化来制备的。大多数实验是用 D-扁桃酸作为起始材料进行的。已经表明所有步骤基本上没有外消旋化。几种制备的 4-吡啶酮衍生物转化为相应的 pyrid-4-yl nonaflates 并进行一系列钯催化的转化，如 Suzuki、Heck 或 Sonogashira 反应。此外，不对称 2,6-二取代吡啶衍生物的区域选择性侧链官能化是通过应用相应吡啶 N-氧化物的 Boekelheide 重排来实现的。所提出的方法为高度取代的对映纯吡啶衍生物提供了一种灵活、快速和可扩展的方法。
• 酒石酸硫酯类化合物及其制备方法和用途
  申请人：江苏奥赛康药业有限公司

  公开号：CN109467527B

  公开（公告）日：2021-04-06

  本发明公开了一种式(I)所示的化合物，其中R1和R2独立地选自任意取代的C1‑6烷基、任意取代的C3‑8环烷基、任意取代的C6‑14芳基、任意取代的‑(CH2)m‑C3‑8环烷基或‑( )n Ar，Ar表示任意取代的C6‑14芳基。所述化合物可用于钛催化的拉唑类硫醚的不对称氧化反应中制备拉唑类药物。
• Synthesis of a library of chiral α-amino acid-based borate counteranions and their application to copper catalyzed olefin cyclopropanation
  作者：David B. Llewellyn、Bruce A. Arndtsen

  DOI：10.1016/j.tetasy.2005.04.004

  日期：2005.5

  Twenty borate counteranions have been prepared from tartaric acid and alpha-amino acid derivatives. Ion pairing of these anions to a copper cation can be Used to induce enantioselectivity into the copper catalyzed cyclopropanation of styrene. Structural modification of the anion provides insight into the importance of each component of the counteranion in asymmetric induction. (C) 2005 Published by Elsevier Ltd.
• Access to Macrocyclic Lactams. Application to a New Series: the Dibenzotetralactams
  作者：N Arnaud

  DOI：10.1016/00404-0399(50)1109u-

  日期：1995.7.31