(E)-4-Bromo-2-pentenoic Acid | 27652-18-2

• 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: (E)-4-Bromo-2-pentenoic Acid
• 英文别名: (E)-4-bromopent-2-enoic acid；(E)-4-Bromo pent-2-en saeure；4-Brompent-2-enoicsaeure；trans-4-bromo-2-pentenoic acid；(+/-)-4-bromo-pent-2t-enoic acid；(+/-)-4-Brom-pent-2t-ensaeure；4-bromo-2-pentenoic acid；4-Bromopent-2-enoic acid
• CAS: 27652-18-2
• 化学式: C₅H₇BrO₂
• 分子量: 179.013
• InChiKey: KDNCGADQPWREDS-NSCUHMNNSA-N

物化性质

• 熔点：
  82-83 °C(Solv: ligroine (8032-32-4))
• 沸点：
  275.4±23.0 °C(Predicted)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-Bromo-2-pentenoic Acid 在 sodium methylate 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 16.75h， 生成 (E)-4-Mercapto-2-pentenoic Acid
  参考文献：
  名称：

  Lithium ammonia reductions of 2-thiophenecarboxylic acids

  摘要：

  DOI：

  10.1021/jo00167a013
• 作为产物：
  描述：

  反式-2-戊烯酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 (E)-4-Bromo-2-pentenoic Acid
  参考文献：
  名称：

  Synthesis of Analogues of GABA. II. 4-Alkyl-4-aminobut-2-enoic Acids and a New Synthesis of Some Vinyl α-Amino Acids

  摘要：

  一系列 制备了一系列 4-烷基-4-氨基丁-2-烯酸 (2)-(5) 作为 GABA 的构象受限类似物。 限制的 GABA 类似物。合成路线包括烯丙基溴化，然后用氨置换 乙烯基甘氨酸类似物(7)-(9)。 反应的副产品。乙烯基甘氨酸类似物 (E)-2-氨基环己基亚基乙酸（4）和(E)-2-氨基环己基亚基乙酸（5）对 GABA 吸收、结合和酶系统的体外生物活性较低。 和 (E)-2-aminocyclopentylideneacetic acid (5) 的体外生物活性较低，这是因为 在有关的特定活性位点上，成环亚甲基的立体阻碍作用。

  DOI：

  10.1071/ch9792507

文献信息

• TETRASUBSTITUTED ALKENE COMPOUNDS AND THEIR USE
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20160347717A1

  公开（公告）日：2016-12-01

  Disclosed herein are compounds, or pharmaceutically acceptable salts thereof, and methods of using the compounds for treating breast cancer by administration to a subject in need thereof a therapeutically effective amount of the compounds or pharmaceutically acceptable salts thereof. The breast cancer may be an ER-positive breast cancer and/or the subject in need of treatment may express a mutant ER-α protein.

  本文披露了化合物或其药学上可接受的盐，以及利用这些化合物治疗乳腺癌的方法，通过向需要治疗的受试者施用这些化合物或其药学上可接受的盐的治疗有效剂量。乳腺癌可能是ER阳性乳腺癌，需要治疗的受试者可能表达突变的ER-α蛋白。
• Synthesis of Analogues of GABA. II. 4-Alkyl-4-aminobut-2-enoic Acids and a New Synthesis of Some Vinyl α-Amino Acids
  作者：RD Allan

  DOI：10.1071/ch9792507

  日期：——

  A series of 4-alkyl-4-aminobut-2-enoic acids (2)-(5) has been prepared as conformationally restricted analogues of GABA. The synthetic route which involved allylic bromination followed by displacement with ammonia also gave vinyl glycine analogues (7)-(9) as readily purified by-products of the reaction. The low biological activity in vitro against GABA uptake, binding and enzyme systems of (E)-2-aminocyclohexylideneacetic acid (4) and (E)-2-aminocyclopentylideneacetic acid (5) has been interpreted in terms of steric hindrance by the ring-forming methylene groups at the particularactive sites concerned.

  一系列 制备了一系列 4-烷基-4-氨基丁-2-烯酸 (2)-(5) 作为 GABA 的构象受限类似物。 限制的 GABA 类似物。合成路线包括烯丙基溴化，然后用氨置换 乙烯基甘氨酸类似物(7)-(9)。 反应的副产品。乙烯基甘氨酸类似物 (E)-2-氨基环己基亚基乙酸（4）和(E)-2-氨基环己基亚基乙酸（5）对 GABA 吸收、结合和酶系统的体外生物活性较低。 和 (E)-2-aminocyclopentylideneacetic acid (5) 的体外生物活性较低，这是因为 在有关的特定活性位点上，成环亚甲基的立体阻碍作用。
• Synthesis of N-substituted oligomers
  申请人：Chiron Corporation

  公开号：US05877278A1

  公开（公告）日：1999-03-02

  A solid-phase method for the synthesis of N-substituted oligomers, such as poly (N-substituted glycines) (referred to herein as poly NSGs) is used to obtain oligomers, such as poly NSGs of potential therapeutic interest which poly NSGs can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two "sub-monomers" directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by --NH.sub.2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a solid support-bound .alpha.-haloacetamide) with a sufficient amount of a second sub-monomer comprising an --NH.sub.2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability. Combinatorial libraries of cyclic compounds are disclosed wherein the cyclic compounds are comprised of at least one ring structure derived from cyclization of a peptoid backbone. The diversity of product compounds is generated by the sequential addition of substituted submonomers. The combinatorial library includes 10 or more, preferably 100 or more, and more preferably 1,000 or more distinct and different compounds. The library includes each of the product compounds in retrievable and analyzable amounts and preferably includes at least one biologically active compound. Methods of synthesizing the combinatorial libraries and assay devices produced using the libraries are disclosed as is methodology for screening for and obtaining biologically active cyclic organic compounds.

  一种固相合成N-取代寡聚物的方法，例如聚(N-取代甘氨酸)（在此处称为聚NSGs），用于获得具有潜在治疗兴趣的寡聚物，例如具有各种侧链取代基的聚NSGs。每个N-取代甘氨酸单体均直接在固定支撑物上由两个“亚单体”组装而成。每个单体添加周期包括两个步骤：（1）用包含能够被-NH.sub.2亲核取代的离去基的酰化试剂（例如卤代乙酸）对与支撑物结合的次级胺进行酰化，以及（2）通过亲核取代离去基（例如卤素，作为固定支撑物上的α-卤代乙酰胺）引入侧链，使用包含足够量第二亚单体的-NH.sub.2基团，例如主要胺，烷氧胺，半羧酸酰，酰基肼，碳酸酯或类似物。重复酰化和取代的两步循环给出所需的寡聚物。使用本方法的自动合成技术高效合成各种寡聚NSGs，使这些寡聚物成为生成和快速筛选各种肽模拟库的有吸引力的候选物。本发明的寡聚物，如N-取代甘氨酸（即聚NSGs），提供了一类在自然界中找不到的肽类化合物，但可以通过合成获得，并且已被证明具有显著的生物活性和蛋白酶稳定性。公开了由至少一个源自肽骨架环化的环结构组成的环化合物的组合库，通过顺序添加取代亚单体生成产物化合物的多样性。组合库包括10个或更多，最好是100个或更多，更好是1,000个或更多不同的化合物。该库中包括每个产物化合物的可检索和可分析量，并且最好包括至少一种具有生物活性的化合物。公开了合成组合库的方法以及使用该库制备的检测装置，以及用于筛选和获得具有生物活性的环状有机化合物的方法。
• Herbicidal 4-((benzimidazol-1-yl)phenoxy)alkanoic acids, esters and salts
  申请人：Shell Oil Company

  公开号：US04439226A1

  公开（公告）日：1984-03-27

  Certain 4-((benzimidazol-1-yl)phenoxy)alkanoic acids, esters and salts, useful as herbicides.

  某些4-((苯并咪唑-1-基)苯氧基)烷酸，酯和盐，可用作除草剂。
• Processes and compounds for preparing histone deacetylase inhibitors and intermediates thereof
  申请人：Helquist Paul

  公开号：US20070021612A1

  公开（公告）日：2007-01-25

  Processes for preparing unsaturated esters useful as intermediates for HDAC inhibitors, by reacting an aldehyde or ketone with compounds having the following formula XX: wherein R 8 is an aliphatic group, an aromatic group, or a combined aliphatic and aromatic group; R 9 and R 10 are each independently hydrogen, an aliphatic group, an aromatic group, a combined aliphatic and aromatic group, or R 10 forms a double bond with L 2 or X 3 ; R 11 and R 12 are each independently an aliphatic group, an aromatic group, or a combined aliphatic and aromatic group; L 2 is an aliphatic linking group, an aromatic linking group, or a combined aliphatic and aromatic linking group; A is P or As; L 2 being selected so that the number of carbon atoms directly in the carbon chain between the R 8 and R 9 groups is at least 4, X 1 and X 2 are each independently O or a single bond, and X 3 is O or forms R 13 and double bond with R 10 , wherein R 13 is an aliphatic group, an aromatic group, or a combined aliphatic and aromatic group.

  制备作为HDAC抑制剂中间体的不饱和酯的过程，通过将醛或酮与具有以下公式XX的化合物反应：其中R8是脂肪基，芳香基或脂肪基和芳香基的组合；R9和R10分别独立地是氢，脂肪基，芳香基，脂肪基和芳香基的组合，或者R10与L2或X3形成双键；R11和R12分别独立地是脂肪基，芳香基或脂肪基和芳香基的组合；L2是脂肪连接基，芳香连接基或脂肪基和芳香基连接基的组合；A是P或As；选择L2使得R8和R9之间的碳链上直接的碳原子数至少为4，X1和X2分别是O或单键，X3是O或与R10形成R13和双键，其中R13是脂肪基，芳香基或脂肪基和芳香基的组合。