2-butene-1,4-diol monoacetate monochloride | 35125-19-0

• 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
• 英文名称: 2-butene-1,4-diol monoacetate monochloride
• 英文别名: (E/Z)-1-acetoxy-4-chloro-2-butene；1-acetoxy-4-chloro-2-butene；1-acetoxy-4-chlorobut-2-ene；4-chlorobut-2-enyl acetete；acetic acid-(4-chloro-but-2-enyl ester)；Essigsaeure-(4-chlor-but-2-enylester)；1-Acetoxy-4-chloro but-2-ene；4-chlorobut-2-enyl acetate
• CAS: 35125-19-0
• 化学式: C₆H₉ClO₂
• 分子量: 148.589
• InChiKey: JGFWVESQVZLCCC-UHFFFAOYSA-N

物化性质

• 沸点：
  82-84.5 °C(Press: 9 Torr)
• 密度：
  1.1510 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-butene-1,4-diol monoacetate monochloride 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成 (Z)-[para-methoxybenzyl(malonyl)amino]but-2-enyl acetate
  参考文献：
  名称：

  Surprisingly Mild “Enolate-Counterion-Free” Pd(0)-Catalyzed Intramolecular Allylic Alkylations

  摘要：

  Palladium-catalyzed intramolecular allylic alkylations of unsaturated EWG-activated amides can take place under phase-transfer conditions or in the presence of a crown ether. These new reaction conditions are milder and higher yielding than those previously reported. A rationalization for such an unexpected result is put forth and validated by DFT-B3LYP calculations. The results suggest cyclization via a counterion-free (E)-enolate TS.

  DOI：

  10.1021/ol047548l
• 作为产物：
  描述：

  1-Acetoxy-4-brom-2-buten 在 Wilkinson's catalyst 、 1,2-二氯乙烷 作用下， 反应 6.0h， 以84%的产率得到2-butene-1,4-diol monoacetate monochloride
  参考文献：
  名称：

  Rhodium-Catalyzed Activation of C(sp³)−X (X = Cl, Br) Bond: An Intermolecular Halogen Exchange Case

  摘要：

  A RhCl(PPh3)(3)-catalyzed halogen-exchange reaction between allyl and alkyl halides with beta-H atoms was observed. The possible mechanism of the reaction involves oxidative addition and reductive elimination of the C(sp(3))-X bonds, which is not common in organometallic chemistry.

  DOI：

  10.1021/ol101995v

文献信息

• Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity
  申请人：Batt G. Douglas

  公开号：US20050192276A1

  公开（公告）日：2005-09-01

  The present application describes modulators of MCP-1 of formula (I): or stereoisomers or pharmaceutically acceptable salts thereof, wherein X, Z, a, b, c, d, bond g, n, s, R 1 , R 2 , R 4 , R 5 , R 10 , R 12 , and R 13 , are as defined above. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis using said modulators are disclosed.

  本申请描述了公式(I)的MCP-1调节剂，或其立体异构体或药学上可接受的盐，其中X、Z、a、b、c、d、键g、n、s、R1、R2、R4、R5、R10、R12和R13如上所定义。此外，还公开了利用这些调节剂治疗和预防哮喘和过敏疾病等炎症性疾病，以及类风湿关节炎和动脉粥样硬化等自身免疫病理的方法。
• Cu(I)-Catalyzed Coupling of (9-Benzylpurin-6-yl)magnesium Chloride with Allyl Halides: An Approach to 6-Allylpurine Derivatives
  作者：Martin Klečka、Tomáš Tobrman、Dalimil Dvořák

  DOI：10.1135/cccc20061221

  日期：——

  6-Allylpurine derivatives are formed by Cu(I)-catalyzed coupling of (9-benzyl-9H-purin-6-yl)- magnesium chloride with allyl halides. The reaction is accompanied by allylic rearrangement in some cases. Under acid conditions the double bond of the allyl group rearranges to the conjugation with purine ring.

  6-烯丙基嘌呤衍生物是由Cu(I)催化下的(9-苄基-9H-嘌呤-6-基)-氯化镁与烯丙基卤化物的偶联反应形成的。在某些情况下，反应伴随着烯丙基重排。在酸性条件下，烯丙基基团的双键会重排到与嘌呤环的共轭位置。
• Kuo, David L., Heterocycles, 1993, vol. 36, # 7, p. 1463 - 1470
  作者：Kuo, David L.

  DOI：——

  日期：——
• Stereo- and regioselective palladium-catalyzed 1,4-acetoxychlorination of 1,3-dienes. 1-Acetoxy-4-chloro-2-alkenes as versatile synthons in organic transformations
  作者：Jan E. Baeckvall、Jan E. Nystroem、Ruth E. Nordberg

  DOI：10.1021/ja00298a043

  日期：1985.6
• Group VI metal carbonyl catalyzed reaction of ethers and acid halides
  作者：Howard Alper、Che-Cheng Huang

  DOI：10.1021/jo00941a012

  日期：1973.1