[(2R,3S)-3-cyclohexyloxiran-2-yl]carboxylic acid | 676324-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: [(2R,3S)-3-cyclohexyloxiran-2-yl]carboxylic acid
• 英文别名: (2R,3S)-2,3-epoxy-3-cyclohexylpropionic acid；(2R,3S)-3-cyclohexyloxirane-2-carboxylic acid
• CAS: 676324-23-5
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: MMFBXEKGRVUOOC-JGVFFNPUSA-N

物化性质

• 沸点：
  311.3±35.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-cyclohexyloxiran-2-yl]carboxylic acid 在 氨 、 N,N-二异丙基乙胺 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Selective C-2 opening of 2,3-epoxyesters with HN3-amine system: A viable route to β-hydroxy-α-amino acids

  摘要：

  The combination of hydrogen azide with amines has proven to effect the C-2 opening of 2,3-epoxyester with high regioselectivity uniformly for trans-epoxyesters and depending on their structures for cis-2,3-epoxyesters.

  DOI：

  10.1016/s0040-4039(00)74855-6
• 作为产物：
  描述：

  3-cyclohexylacrylic acid 在 titanium(IV) isopropylate 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 D-(-)-酒石酸二乙酯 、 过氧化氢异丙苯 、 硫酸 、 三氧化硫吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 生成 [(2R,3S)-3-cyclohexyloxiran-2-yl]carboxylic acid
  参考文献：
  名称：

  Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate

  摘要：

  Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compound 2. Structural hybridation of 4 with the orally available analog 5 resulted in another orally-available spirodiketopiperazine CCR5 antagonist 6a that possesses more favorable pharmaceutical profile for use as a drug candidate. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.109

文献信息

• New chiral amino alcohol ligands for catalytic enantioselective addition of diethylzincs to aldehydes
  作者：Carla Sappino、Alessandra Mari、Agnese Mantineo、Mauro Moliterno、Matteo Palagri、Chiara Tatangelo、Lorenza Suber、Paolo Bovicelli、Alessandra Ricelli、Giuliana Righi

  DOI：10.1039/c8ob00165k

  日期：——

  applicability as chiral catalysts was evaluated by carrying out the same reaction on a family of aldehydes, including variously substituted aromatic ones as well as an aliphatic analogue. The results have confirmed the validity of the fine-tuning process performed on ligands 13a and 13b. In fact, both exhibited excellent catalytic activity as demonstrated by the chemical yields and ee obtained from all the

  已经进行了旨在合成和优化具有适合于固定在磁铁矿纳米颗粒上的结构的新型，光学活性的β-氨基醇配体的结构的研究。优化的均相氨基醇催化剂13a和13b的手性来自合适的烯丙醇的Sharpless环氧化反应，通过使用公认的对映选择性氨基醇促进的二乙基锌与苯甲醛的加成反应进行测试，得到相应的苯甲醇，收率基本定量，ee = 95％。然后，通过对一系列醛，包括各种取代的芳族醛以及脂族类似物进行相同的反应，评估了它们作为手性催化剂的广泛适用性。结果证实了对配体13a和13b进行的微调过程的有效性。。实际上，如从化学产率和从所有测试的醛获得的ee所证实的，两者均显示出优异的催化活性，几乎与芳环中取代的位置和类型无关。
• Optically active epoxy compounds and processes for their production
  申请人：TOSOH CORPORATION

  公开号：US20040063979A1

  公开（公告）日：2004-04-01

  An optically active epoxyenone derivative of the following formula (1): 1 wherein R 1 is a methyl group, an ethyl group or a C 3-10 branched, linear or cyclic alkyl group, and R 2 is a phenyl group, a substituted phenyl group or a tert-butyl group.

  以下是式子（1）的光学活性环氧酮衍生物：1其中R1为甲基基团、乙基基团或C3-10支链、线性或环状烷基团，R2为苯基、取代苯基或叔丁基。
• Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist
  作者：Rena Nishizawa、Toshihiko Nishiyama、Katsuya Hisaichi、Chiaki Minamoto、Masayuki Murota、Yoshikazu Takaoka、Hisao Nakai、Hideaki Tada、Kenji Sagawa、Shiro Shibayama、Daikichi Fukushima、Kenji Maeda、Hiroaki Mitsuya

  DOI：10.1016/j.bmc.2011.05.022

  日期：2011.7

  Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented. (C) 2011 Elsevier Ltd. All rights reserved.
• JP2004284992A
  申请人：——

  公开号：JP2004284992A

  公开（公告）日：2004-10-14
• US7169944B2
  申请人：——

  公开号：US7169944B2

  公开（公告）日：2007-01-30