(E)-hex-3-deutero-2-enoic acid | 950842-25-8

• 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)-hex-3-deutero-2-enoic acid
• 英文别名: 3-deutero-(E)-hex-2-enoic acid；(E)-3-deuteriohex-2-enoic acid
• CAS: 950842-25-8
• 化学式: C₆H₁₀O₂
• 分子量: 115.136
• InChiKey: NIONDZDPPYHYKY-NWUMDMOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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)-hex-3-deutero-2-enoic acid 、 环丙胺 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以65%的产率得到(E)-N-cyclopropylhex-3-deutero-2-enamide
  参考文献：
  名称：

  Deuterated hepatitis C protease inhibitors

  摘要：

  一种氘代的α-酮氨基立体特异化合物，其化学式为其中D表示立体特异碳原子上的一个氘原子。

  公开号：

  US20070225297A1
• 作为产物：
  描述：

  (E)-hex-3-deutero-2-enal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.5h， 以75%的产率得到(E)-hex-3-deutero-2-enoic acid
  参考文献：
  名称：

  Deuterated hepatitis C protease inhibitors

  摘要：

  一种氘代的α-酮氨基立体特异化合物，其化学式为其中D表示立体特异碳原子上的一个氘原子。

  公开号：

  US20070225297A1

文献信息

• Process for preparing optically enriched compounds
  申请人：Vertex Pharmceuticals Incorporated

  公开号：EP2194039A1

  公开（公告）日：2010-06-09

  This invention relates to a process for preparing a compound of Formula 1 wherein: the carbon atoms alpha and beta to the carboxy group are stereocenters; R1 is independently H, optionally substituted aliphatic, optionally substituted cycloaliphatic, optionally substituted arylaliphatic, optionally substituted heteroaliphatic or optionally substituted heteroarylaliphatic; R'1 is deuterium such that the deuterium enrichment is at least 50%; R'2 is -NHR2 or -OE; R2 is H, optionally substituted aliphatic, optionally substituted cycloaliphatic, optionally substituted arylaliphatic, optionally substituted heteroaliphatic or optionally substituted heteroarylaliphatic; and E is C1-6 alkyl or benzyl; wherein the process comprises the steps of: a) forming a salt of a compound of Formula 1, and b) crystallizing said salt to give a compound of greater than 55% enantiomeric excess.

  本发明涉及一种制备式 1 化合物的工艺 其中 羧基的碳原子α和β是立体中心； R1 独立地为 H、任选取代的脂肪族、任选取代的环脂族、任选取代的芳脂族、任选取代的杂脂族或任选取代的杂芳脂族； R'1 是氘，氘富集度至少为 50%； R'2 是-NHR2 或-OE； R2 是 H、任选取代的脂肪族、任选取代的环脂族、任选取代的芳脂族、任选取代的杂脂族或任选取代的杂芳脂族；以及 E 是 C1-6 烷基或苄基； 其中该工艺包括以下步骤 a) 形成式 1 化合物的盐，和 b) 结晶所述盐，得到对映体过量率大于 55%的化合物。
• In Vitro and In Vivo Isotope Effects with Hepatitis C Protease Inhibitors: Enhanced Plasma Exposure of Deuterated Telaprevir versus Telaprevir in Rats
  作者：François Maltais、Young Chun Jung、Minzhang Chen、Jerry Tanoury、Robert B. Perni、Nagraj Mani、Leena Laitinen、Hui Huang、Shengkai Liao、Hongying Gao、Hong Tsao、Eric Block、Chien Ma、Rebecca S. Shawgo、Christopher Town、Christopher L. Brummel、David Howe、S. Pazhanisamy、Scott Raybuck、Mark Namchuk、Youssef L. Bennani

  DOI：10.1021/jm901023f

  日期：2009.12.24

  Telaprevir 2 (VX-950), an inhibitor of the hepatitis C virus (HCVa) NS3-4A protease, is in phase 3 clinical trials. One of the major metabolites of 2 is its P1-(R)-diastereoisomer, 3 (VRT-394), containing an inversion at the chiral center next to the alpha-ketoamide on exchange of a proton with solvent. Compound 3 is approximately 30-fold less active against HCV protease. In an attempt to suppress the epimerization of 2 without losing activity against the HCV protease, the proton at that chiral site was replaced with deuterium (d). The compound 1 (d-telaprevir) is as efficacious as 2 in in vitro inhibition of protease activity and viral replication (replicon) assays. The kinetics of in vitro stability of 1 and 2 in buffered pH solutions and plasma samples, including human plasma, suggest that 1 is significantly more stable than 2. Oral administration (10 mg/kg) in rats resulted in a similar to 13% increase of AUC for 1.
• DEUTERATED HEPATITIS C PROTEASE INHIBITORS
  申请人：Vertex Pharmceuticals Incorporated

  公开号：EP1993994A2

  公开（公告）日：2008-11-26
• COMPOSITIONS AND RELATED METHODS FOR AGRICULTURE
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US20210289794A1

  公开（公告）日：2021-09-23

  The invention comprises methods for decreasing colonization by a bacterium of a gut of a stink bug, the method comprising providing a composition comprising vanillin or an analog thereof; and delivering said composition to an egg from which the stink bug will hatch, whereby colonization by the bacterium within the gut of the stink bug hatched from the egg treated with the composition is decreased relative to a stink bug hatched from an untreated egg. In some embodiments, the decrease in colonization by the bacterium decreases the fitness of the stink bug, e.g., decreases reproductive ability, survival, rate of development, number of eggs, number of hatched eggs, adult emergence rate, body length, body width, body mass, or cuticle thickness. In some embodiments of the methods herein, the bacterial colonization-disrupting agent is an inhibitor of bacterial metabolism. In some embodiments, the bacterial colonization-disrupting agent is a polyhydroxyalkanoate (PHA) synthesis inhibitor.
• US8247532B2
  申请人：——

  公开号：US8247532B2

  公开（公告）日：2012-08-21