(1S,3R,4S)-3,4-二羟基环戊烷e羧酸 | 39798-11-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: (1S,3R,4S)-3,4-二羟基环戊烷e羧酸
• 英文名称: (1R,3R,4S)-3,4-dihydroxycyclopentanecarboxylic acid
• 英文别名: rac-(1S,3R,4S)-3,4-dihydroxycyclopentane-1-carboxylic acid；3-t.4-t-Dihydroxy-1.r-cyclopentancarbonsaeure
• CAS: 39798-11-3
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: NPAXFZBGZWAVIF-ZGQXEFDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.76
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S)-3,4-二羟基环戊烷e羧酸 、 2,2-二甲氧基丙烷 在 (+)-10-camphorsulfonic acid 作用下， 以 环己烷 、 二甲基亚砜 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Insights into the Formation of Symmetrical Trimers of Dialkylated Ketenes Starting from Acid Chloride Precursors

  摘要：

  Application of known dialkyl ketene di- and trimerization to more complex precursors could readily open the route to highly functionalized symmetrical cyclobuta-1,3-diones and cyclohexa-1,3,5-triones. We report herein the results on three substrates containing either a C=C double bond or a protected glycol moiety as illustrative functionalized groups. The nature of the substituents is found to be crucial: while cyclopentenyl and more constrained dioxolanocyclopentenyl precursors efficiently dimerize, a diallylic derivative fails. At the millimolar scale, methoxide-catalyzed trimerization shows limited reproducibility, even for the reported substrate tetramethylcyclobuta-1,3-dione. However, systematic studies, including the use of microwaves, demonstrate that formation of symmetrical trimers is favored under solvent-free conditions and conventional heating, which allowed us to isolate and characterize trispiro[4.1.4.1.4.1]octadeca-2,9,15-triene-6,12,18-trione.

  DOI：

  10.1007/s00706-007-0689-z
• 作为产物：
  描述：

  methyl 2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxole-5-carboxylate 在 水 、 对甲苯磺酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (1S,3R,4S)-3,4-二羟基环戊烷e羧酸
  参考文献：
  名称：

  [EN] ANTIMICROBIAL AGENTS
  [FR] AGENTS ANTIMICROBIENS

  摘要：

  这项发明提供了恩氨环素Ha的新型类似物及其药学上可接受的盐、代谢物、同分异构体（例如立体异构体）和前药。这些化合物在治疗由革兰氏阴性细菌引起的感染方面具有有效性，如包括鲍曼不动杆菌在内。符合该发明的化合物包括式（A）的化合物及其药学上可接受的盐、代谢物、同分异构体（例如立体异构体）和前药：在式（A）中：X为0或NRx（其中R*为H或C1-3烷基，例如CH3）；R1为一个5-或6-成员的、饱和或不饱和的、碳环，可选择地由一个或多个取代基取代，或R1为一个可选择地取代的直链或支链C-1-6烷基基团（例如C1-3烷基基团）；R2为H、F、Cl、Br、I或CH3；R3为H或OH；R8为一个直链或支链C1-8烷基基团（例如C1-6烷基基团）；Y为以下各组中的一个：（其中每个*表示该组与分子其余部分的连接点；R9为H、F、Cl、Br或I；R4和R5分别独立选择自H和OH，或R4和R5一起为=0，优选R4为H且R5为OH；R6为H、F、Cl、Br、I或CH3；R7为H且R7'为OH，或R7和R7'一起为=0，优选R7为H且R7'为OH）；每个—独立表示一个可选键（即C2-C3、C4-C5、C6-C7、C8-C9和C10-C11中的每一个独立地是C-C（单）或C=C（双）键）。

  公开号：

  WO2018193273A1

文献信息

• ANTIMICROBIAL AGENTS
  申请人：THE UNIVERSITY OF WARWICK

  公开号：US20200048183A1

  公开（公告）日：2020-02-13

  The invention provides novel analogues of enacyloxin Ha and their pharmaceutically acceptable salts, metabolites, isomers (e.g. stereoisomers) and prodrugs. Such compounds are effective in the treatment of infections caused by Gram-negative bacteria such as Acinetobacter baumannii . Compounds in accordance with the invention include those of formula (A), and their pharmaceutically acceptable salts, metabolites, isomers (e.g. stereoisomers) and prodrugs: In formula (A): X is 0 or NR x (where R* is either H or C 1-3 alkyl, e.g. CH 3 ); R 1 is a 5- or 6-membered, saturated or unsaturated, carbocyclic ring optionally substituted by one or more substituents, or R 1 is an optionally substituted straight-chained or branched C 1-6 alkyl group (e.g. C 1-3 alkyl group); R 2 is H, F, Cl, Br, I or CH 3 ; R 3 is H or OH; R 8 is a straight-chained or branched C 1-8 alkyl group (e.g. a C 1-6 alkyl group); Y is one of the following groups: (wherein each * denotes the point of attachment of the group to the remainder of the molecule; R 9 is H, F, Cl, Br or I; R 4 and R 5 are independently selected from H and OH, or R 4 and R 5 together are =0, preferably R 4 is H and R 5 is OH; R 6 is H, F, Cl, Br, I or CH 3 ; R 7 is H and R 7′ is OH, or R 7 and R 7′ together are =0, preferably R7 is H and R7′ is OH); and each — independently represents an optional bond (i.e. each of C 2 -C 3 , C 4 -C 5 , C 6 -C 7 , C 8 -C 9 and C 10 -C 11 are independently either C—C (single) or C═C (double) bonds).