4-(2-cyclopentenyl)butanoic acid | 163444-09-5

• 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: 4-(2-cyclopentenyl)butanoic acid
• 英文别名: 4-(cyclopent-2-en-1-yl)butanoic acid；4-(cyclopent-2-enyl)butanoic acid；4-cyclopent-2-enyl-butyric acid；4-Cyclopent-2-enyl-buttersaeure；γ-(Δ²-Cyclopentenyl)-buttersaeure；4-Cyclopent-2-en-1-ylbutanoic acid；4-cyclopent-2-en-1-ylbutanoic acid
• CAS: 163444-09-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: QADIPHCFWXNJIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4-(2-cyclopentenyl)butanoic acid 在 氢氧化钾 、 偶氮二异丁腈 、 三氯溴甲烷 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 16.5h， 生成 cis and trans N-methyl-N-phenyl-cis-bicyclo<3.3.0>octane-2-carboxamide
  参考文献：
  名称：

  Amide-based protecting/radical translocating (PRT) groups. Generation of radicals adjacent to carbonyls by 1,5-hydrogen transfer reactions of o-iodoanilides

  摘要：

  The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best ''protecting/radical translocating'' (PRT) groups introduced to date. Beyond its good performance in radical translocation reactions, it is easy to introduce, serves as a reasonable protecting group both before and after the translocation, and (with appropriate modifications) is easy to remove.

  DOI：

  10.1016/s0040-4020(01)90466-1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 4-(2-cyclopentenyl)butanoic acid
  参考文献：
  名称：

  Burschkies; Scholl, Chemische Berichte, 1949, vol. 82, p. 224

  摘要：

  DOI：

文献信息

• Stereocontrolled Synthesis of Substituted Bicyclic Ethers through Oxy-Favorskii Rearrangement: Total Synthesis of (±)-Communiol E
  作者：Shoji Kobayashi、Tatsuhiro Kinoshita、Takuji Kawamoto、Masato Wada、Hiroyuki Kuroda、Araki Masuyama、Ilhyong Ryu

  DOI：10.1021/jo201064h

  日期：2011.9.2

  The potential of the oxy-Favorskii rearrangement to form branched cis-fused bicyclic ethers was explored. Both tertiary and quaternary centers were constructed in highly stereospecific manners. Methanol and primary amines were effective nucleophiles for the rearrangement. The total synthesis of (±)-communiol E was achieved based on this method.

  探索了氧基-Favorskii重排形成支链顺式稠合双环醚的潜力。三级和四级中心都是以高度立体化的方式构建的。甲醇和伯胺是有效的重排亲核试剂。基于该方法，实现了（±）-香酚E的全合成。
• Total Synthesis of Δ¹²-Prostaglandin J₃: Evolution of Synthetic Strategies to a Streamlined Process
  作者：K. C. Nicolaou、Kiran Kumar Pulukuri、Ruocheng Yu、Stephan Rigol、Philipp Heretsch、Charles I. Grove、Christopher R. H. Hale、Abdelatif ElMarrouni

  DOI：10.1002/chem.201601449

  日期：2016.6.13

  cross‐conjugated dienone structural motif of 1 was forged by an aldol reaction/dehydration sequence from key building blocks enone 13 and aldehyde 14, whose lone stereocenters were generated by an asymmetric Tsuji–Trost reaction and an asymmetric Mukaiyama aldol reaction, respectively. During this program, a substituent‐governed regioselectivity pattern for the Rh‐catalyzed C−H functionalization of cyclopentenes

  Δ的总合成12 -前列腺素Ĵ 3（Δ 12 -PGJ 3，1），所报告的白血病干细胞消融器，通过若干战略和战术进行说明。关键的共轭烯酮13和醛14的醛醇缩合反应/脱水序列伪造了1的标志性交叉共轭二烯酮结构基序。，其单独的立体中心分别由不对称的Tsuji-Trost反应和不对称的Mukaiyama aldol反应产生。在该程序中，发现了用于Rh催化的环戊烯和相关烯烃的CH官能化的取代基控制的区域选择性模式。1的合成从最初的策略发展到最终的简化流程，这是通过改进片段13和14的结构，探索迄今未充分利用的手性内酯合成子57的化学性质以及环戊烯酮中间体的非对映选择性烷基化来进行的。 。所描述的化学设置了大规模生产Δ的阶段12 -PGJ3并设计类似物用于进一步的生物学和药理研究。
• Arvin; Adams, Journal of the American Chemical Society, 1928, vol. 50, p. 1792
  作者：Arvin、Adams

  DOI：——

  日期：——
• Amide-based protecting/radical translocating (PRT) groups. Generation of radicals adjacent to carbonyls by 1,5-hydrogen transfer reactions of o-iodoanilides
  作者：Dennis P. Curran、Hosung Yu、Hongtao Liu

  DOI：10.1016/s0040-4020(01)90466-1

  日期：——

  The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best ''protecting/radical translocating'' (PRT) groups introduced to date. Beyond its good performance in radical translocation reactions, it is easy to introduce, serves as a reasonable protecting group both before and after the translocation, and (with appropriate modifications) is easy to remove.
• Burschkies; Scholl, Chemische Berichte, 1949, vol. 82, p. 224
  作者：Burschkies、Scholl

  DOI：——

  日期：——