(R)-4-(4-chlorophenyl)-1,3-dioxolan-2-one | 191109-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4-(4-chlorophenyl)-1,3-dioxolan-2-one
• 英文别名: (4R)-4-(4-chlorophenyl)-1,3-dioxolan-2-one
• CAS: 191109-44-1
• 化学式: C₉H₇ClO₃
• 分子量: 198.606
• InChiKey: ZPRQKRGNDGAETC-QMMMGPOBSA-N

物化性质

• 沸点：
  382.7±42.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-(4-chlorophenyl)-1,3-dioxolan-2-one 在 lithium aluminium tetrahydride 、 sodium azide 、 水 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 2-(Bis-{[(S)-1-(4-chloro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-amino)-N-[(S)-1-(4-chloro-phenyl)-2-hydroxy-ethyl]-acetamide
  参考文献：
  名称：

  Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst

  摘要：

  Optically active copper(II)-tris(oxazoline) complex that was synthesized as a model compound of the active site of non-heme oxygenase, was found to catalyze allylic oxidation of cycloalkenes to give the corresponding 2-cycloalkenyl benzoates with moderate to excellent enantioselectivity (up to 93% ee) under the Kharash-Sosnovsky reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00322-0
• 作为产物：
  描述：

  4-氯苯乙烯 在 sodium hydroxide 、 potassium osmate(VI) 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 生成 (R)-4-(4-chlorophenyl)-1,3-dioxolan-2-one
  参考文献：
  名称：

  Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst

  摘要：

  Optically active copper(II)-tris(oxazoline) complex that was synthesized as a model compound of the active site of non-heme oxygenase, was found to catalyze allylic oxidation of cycloalkenes to give the corresponding 2-cycloalkenyl benzoates with moderate to excellent enantioselectivity (up to 93% ee) under the Kharash-Sosnovsky reaction conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00322-0

文献信息

• Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide
  作者：Tadashi Ema、Maki Yokoyama、Sagiri Watanabe、Sota Sasaki、Hiromi Ota、Kazuto Takaishi

  DOI：10.1021/acs.orglett.7b01838

  日期：2017.8.4

  Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of

  在合成的手性大环化合物1中，具有3,5-双（三氟甲基）苯基乙炔基的1m是从二取代或单取代的环氧化物和CO 2对映选择性合成环状碳酸酯的最佳有机催化剂。1m的X射线晶体结构揭示了一个明确定义的手性腔，带有多个氢键位，适用于环氧化物的对映选择性活化。提议的催化循环得到DFT计算的支持。
• Nitrene‐Mediated C−H Oxygenation: Catalytic Enantioselective Formation of Five‐Membered Cyclic Organic Carbonates
  作者：Xin Nie、Chen‐Xi Ye、Sergei I. Ivlev、Eric Meggers

  DOI：10.1002/anie.202211971

  日期：2022.11.25

  A new strategy for the synthesis of non-racemic cyclic carbonates from abundant alcohol feedstocks is presented. The method exploits an unusual nitrene-mediated C−H oxygenation via a proposed 1,7-hydrogen atom transfer (HAT).

  提出了一种从丰富的酒精原料中合成非外消旋环状碳酸酯的新策略。该方法通过拟议的 1,7-氢原子转移 (HAT) 利用不寻常的氮烯介导的 C−H 氧化作用。
• Reaction of 1,2-Cyclic Sulfites with Some Soft Nucleophiles. Formation of Enantiomerically Pure gamma-Lactones.
  作者：Kirsten Nymann、John S. Svendsen、Eli Ranes、Jaroslav Riha、Eugen Mesaros、Alin Mihis、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0338

  日期：——

  The reaction between 1,2-cyclic sulfites and soft carbon centered nucleophiles has been investigated. For monosubstituted cyclic sulfites, the main products were gamma-lactones or acetoxy esters. For 1,2-disubstituted cyclic sulfites. cyclopropanes. carbonate and dioxolanes were the main products, A mechanistic rationale for the product formation is presented.