((1R,2R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropyl)methanol | 203498-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1R,2R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropyl)methanol
• 英文别名: [(1R,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropyl]methanol
• CAS: 203498-03-7
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: AUDQJVXATOSXSF-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((1R,2R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropyl)methanol 在 N,N-二异丙基乙胺 、 三氧化硫吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.42h， 以71%的产率得到(1R,2R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropane-1-carbaldehyde
  参考文献：
  名称：

  LpxC抑制剂前导化合物的优化，着重于高剂量静脉给药的功效和配方。

  摘要：

  LpxC抑制剂从具有有限功效和溶解度的先导化合物开始进行了优化，目的是为医院环境中革兰氏阴性病原体引起的严重感染的治疗提供新的选择。为了能够开发用于高剂量静脉内给药的水性制剂，早期就优先考虑了体内溶解性和抗菌活性的改善。该前导优化程序导致发现诸如13和30的化合物，它们在动物感染模型中显示出高溶解性和针对革兰氏阴性病原体的有效功效。

  DOI：

  10.1021/acs.jmedchem.9b01605
• 作为产物：
  描述：

  (1E,4'S)-3-[(tert-Butyldiphenylsilyl)oxy]-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-propene 在 四丁基氟化铵 、 diethylzinc 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ((1R,2R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropyl)methanol
  参考文献：
  名称：

  关于苏糖内酯总合成的研究：环丙烷-内酯链段的立体选择性合成

  摘要：

  已经开发了一种简单的立体选择路线，以合成茄醛酸内酯的右手片段，在该方法中，首先合成关键的双功能环丙烷中间体2，然后以良好的总收率构建了八元内酯环。

  DOI：

  10.1016/s0040-4039(97)10731-6

文献信息

• [EN] SUBSTITUTED 1,2-DIHYDRO-3H-PYRROLO[1,2-C]IMIDAZOL-3-ONE ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS 1,2-DIHYDRO-3H-PYRROLO[1,2-C]IMIDAZOL-3-ONE SUBSTITUÉS
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2017037221A1

  公开（公告）日：2017-03-09

  The invention relates to antibacterial compounds of formula (I) wherein M is one of the groups MA, MB and MC represented below wherein R1, MA, MB and MC are as defined in the specification; and to salts thereof.

  该发明涉及公式（I）中的抗菌化合物，其中M是下面所表示的MA、MB和MC中的一种基团，其中R1、MA、MB和MC如规范中所定义；以及其盐。
• The synthesis of single enantiomers of meromycolic acids from mycobacterial wax esters
  作者：Juma'a R. Al Dulayymi、Mark S. Baird、Evan Roberts、David E. Minnikin

  DOI：10.1016/j.tet.2006.09.019

  日期：2006.12

  Three stereoisomers of a wax ester meromycolate have been prepared starting from mannitol. A detailed comparison of their NMR spectra with those reported for a homologous series of natural wax esters allows the relative configurations of the α-methyl group and adjacent trans-cyclopropane to be determined.

  从甘露糖醇开始已经制备了蜡酯巯基甲酸酯的三种立体异构体。将它们的NMR光谱与天然蜡酯的同源系列报道的NMR光谱进行详细比较，可以确定α-甲基和相邻的反式-环丙烷的相对构型。
• Substituted 1,2-dihydro-3H-pyrrolo[1,2-c]imidazol-3-one antibacterial compounds
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：US10314823B2

  公开（公告）日：2019-06-11

  The invention relates to antibacterial compounds of formula I wherein M is one of the groups MA, MB and MC represented below wherein R1, MA, MB and MC are as defined in the specification; and to salts thereof.

  本发明涉及式 I 的抗菌化合物 其中 M 是下表所代表的基团 MA、MB 和 MC 之一 其中 R1、MA、MB 和 MC 如说明书中所定义； 及其盐类。
• The first asymmetric total syntheses of 3((1R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid
  作者：Debendra K. Mohapatra、Nagesh Guguloth、J.S. Yadav

  DOI：10.1016/j.tetlet.2012.09.133

  日期：2012.12

  The first efficient total syntheses of 3((1 R,2R)- and 3((1S,2R)-2-(12-methyltridecyl)cyclopropyl)propanoic acid have been achieved following a chelation controlled modified Simmon-Smith cyclopropanation, Wittig reaction, Horner-Wadsworth-Emmons olefination, and p-toluenesulfonyl hydrazide catalyzed hydrogenation as key reactions in good overall yield. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of optically active cis- and trans-1,2-disubstituted cyclopropane derivatives by the Simmons-Smith reaction of allyl alcohol derivatives derived from (R)-2,3-O-isopropylideneglyceraldehyde
  作者：Tsutomu Morikawa、Hirofumi Sasaki、Ryo Hanai、Akira Shibuya、Takeo Taguchi

  DOI：10.1021/jo00080a017

  日期：1994.1

  The Simmons-Smith reactions of Z- and E-allyl alcohol derivatives 6 derived from (R)-2,3-O-isopropylideneglyceraldehyde (5) were used for the synthesis of optically active cis- and trans-1,2 disubstituted cyclopropane derivatives. Reaction of 6 with diethyl zinc and diiodomethane gave cyclopropane derivatives 7 in 84% to quantitative yields with 35 to approximate to 100% des. Identical facial selectivities toward the double bonds, Ire-asi for Z-6 and 1re-2re for E-6, were observed in the cyclopropanations. The diastereoselectivity was dependent on the protecting group on the terminal allylic oxygen (R of 6, TBDPS > MOM > Bn) and on the stereochemistry of the double bond (Z > E). For TBDPS ethers Z- and E-6c, cis- and trans-7c were obtained as single diastereomers respectively. It was clearly demonstrated that the stereoselectivity of the cyclopropanation is controlled by the directing effect of the allylic oxygen (O-1) of the dioxolane ring which coordinates to the reagent. The terminal allylic oxygen (O-2) lowered the diastereoselectivity This reaction was applied to the synthesis of optically active cyclopropane analogs of gamma-aminobutyric acid (GABA) 18, 22, and ent-22.