(2E,4E)-5-cyclohexylpenta-2,4-dienoyl chloride | 175552-85-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (2E,4E)-5-cyclohexylpenta-2,4-dienoyl chloride
• CAS: 175552-85-9
• 化学式: C₁₁H₁₅ClO
• 分子量: 198.692
• InChiKey: WYSZJERAUOVCFU-KBXRYBNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-cyclohexylpenta-2,4-dienoyl chloride 在 吡啶 、 4-二甲氨基吡啶 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2E,4E)-5-cyclohexyl-N-(6,6-dimethoxy-3-oxocyclohexa-1,4-dien-1-yl)penta-2,4-dienamide
  参考文献：
  名称：

  The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

  摘要：

  DOI：

  10.1055/s-1998-2064
• 作为产物：
  描述：

  (2E,4E)-5-cyclohexylpenta-2,4-dienoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 生成 (2E,4E)-5-cyclohexylpenta-2,4-dienoyl chloride
  参考文献：
  名称：

  The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

  摘要：

  DOI：

  10.1055/s-1998-2064

文献信息

• The synthesis of novel analogues of the manumycin family of antibiotics and the antitumour antibiotic LL-C10037α
  作者：Isabelle Kapfer、Norman J. Lewis、Gregor Macdonald、Richard J.K. Taylor

  DOI：10.1016/0040-4039(96)00203-1

  日期：1996.3

  Efficient approaches to the central amino-epoxycyclohexenone core of the manumycin family of antibiotics are described. The use of this methodology to prepare the antitumour antibiotic LL-C10037α and its epimer, both in racemic form, and a number of analogues of manumycin, alisamycin and asukamycin, lacking the C-4 substituent, are then outlined.

  描述了对manumycin家族的中央氨基-环氧-环己烯酮核心的有效方法。然后概述了使用该方法制备外消旋形式的抗肿瘤抗生素LL-C10037α及其差向异构体，以及许多缺少C-4取代基的Manumycin，alisamycin和Asukamycin的类似物的方法。
• PARA-QUINOL DERIVATIVES AND METHODS OF STEREO SELECTIVELY SYNTHESIZING AND USING SAME
  申请人：Plourde Guy L.

  公开号：US20090318548A1

  公开（公告）日：2009-12-24

  This application relates to para-quinol derivatives, such as analogues of manumycins, aranorosins and gymnastatins. This application also relates to methods of synthesizing and using the para-quinol derivatives. In one embodiment of the invention a compound having the chemical structure (I) is provided wherein X 1 and X 2 are carbon atoms either joined by double bond or joined by a single bond and comprising constituents of an epoxide ring or a hydroxyethylene moiety; X 3 and X 4 are carbon atoms either joined by double bond or joined by a single bond and comprising constituents of an epoxide ring; R 1 is selected from the group consisting of branched alkyl chains, unbranched alkyl chains, cycloalkyl groups, aromatic groups, alcohols, ethers, amines, and substituted or unsubstituted ureas, esters, aldehydes and carboxylic acids; and R 2 is selected from the group consisting of H, OH and NHR 3 wherein R 3 is a nitrogen protecting group. In a particular embodiment of the invention R 1 is a polyunsaturated carbon chain as found in biologically active manumycins. The applicant's synthetic method may involve diasteroselective formation of a spirolactone in an oxidative spiroannulation process using tyrosine or a tyrosine derivative having a chiral centre as a starting material.

  本申请涉及对位喹啉衍生物，例如曼纽霉素、阿拉诺罗辛和体操霉素的类似物。本申请还涉及合成和使用对位喹啉衍生物的方法。在发明的一个实施例中，提供了具有化学结构（I）的化合物，其中X1和X2是由双键连接或单键连接的碳原子，并包括环氧环或羟基乙烯基的组分；X3和X4是由双键连接或单键连接的碳原子，并包括环氧环的组分；R1选自支链烷基链，直链烷基链，环烷基团，芳香族团，醇，醚，胺和取代或未取代的脲、酯、醛和羧酸；R2选自H，OH和NHR3，其中R3是氮保护基。在发明的一个特定实施例中，R1是生物活性曼纽霉素中发现的多不饱和碳链。申请人的合成方法可能涉及使用酪氨酸或手性中心的酪氨酸衍生物作为起始材料，在氧化螺环化过程中二面体选择性地形成螺内酯。
• The first total synthesis of a member of the manumycin family of antibiotics: Alisamycin
  作者：Lilian Alcaraz、Gregor Macdonald、Isabelle Kapfer、Norman J. Lewis、Richard J.K. Taylor

  DOI：10.1016/0040-4039(96)01414-1

  日期：1996.9

  The development of a general synthetic route to the manumycin family of antibiotics is described and exemplified by the first total synthesis of alisamycin in racemic form.

  迈努霉素系列抗生素的一般合成路线的开发已通过外消旋形式的阿里霉素的第一个全合成进行了描述和举例说明。
• Total Synthesis of (±)-Nisamycin
  作者：Peter Wipf、Philip D. G. Coish

  DOI：10.1021/jo990413m

  日期：1999.7.1

  We have developed a highly convergent synthesis of the manumycin-type m-C7N-antibiotic nisamycin that is applicable to other members of this family of antibiotics. The synthesis features a three-step sequence to the epoxyquinol core that serves as a scaffold for the attachment of the polyene side chains. The eastern polyene side chain was constructed via a novel organozirconocene-mediated synthesis. Zirconocene methodology was also applied to the synthesis of the polyene side chains of asukamycin. The southern side chain of nisamycin was introduced via a Stille reaction that employed a vinyl bromo ketone, derived from an acid-sensitive bromo ketal. Pd-mediated coupling of the vinyl bromide with a stannyl TIPS ester gave TIPS-protected nisamycin that was readily converted to the natural product.
• Asymmetric synthesis of the mC7N core of the manumycin family: Preparation of (+)-MT 35214 and a formal total synthesis of (−)-alisamycin
  作者：Gregor Macdonald、Lilian Alcaraz、Norman J Lewis、Richard J.K Taylor

  DOI：10.1016/s0040-4039(98)01047-8

  日期：1998.7

  An asymmetric approach to the mC(7)N epoxyquinone central unit of the manumycin antibiotics is described based on the enantioselective (89% ee) chiral phase transfer epoxidation of a substituted cyclohexenone. The chiral epoxide is employed in the first syntheses of the tide compounds in enantiomerically pure form. (C) 1998 Elsevier Science Ltd. All rights reserved.