4-(benzyloxy)-3-hydroxybutanenitrile | 137618-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(benzyloxy)-3-hydroxybutanenitrile
• 英文别名: 3-hydroxy-4-phenylmethoxybutanenitrile
• CAS: 137618-52-1
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: JEGNUZIGCHAVNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  384.9±32.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-3-hydroxybutanenitrile 在 三甲基氯硅烷 、 甲烷磺酸 、 Arthrobacter sp. lipase 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 29.0h， 生成 tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate
  参考文献：
  名称：

  Efficient lipase-catalyzed kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles: application to an expedient synthesis of a statin intermediate

  摘要：

  The kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles was investigated by lipase-catalyzed transesterification in organic solvents. A high enantio selectivity was obtained via reaction with vinyl acetate in a mixed solvent (n-heptane/acetonitrile 1:1), which was catalyzed by the lipase from Artgribacter sp. A better selectivity was demonstrated when the number of substituents on the aryl ring increased. (S)-4-Arylmethoxy-3-hydroxybutanenitriles can be obtained with enantiomeric excesses of up to 98.0% by this method. Furthermore we have developed a novel route to synthesize tert-butyl (S)-6-benzyloxy-5-hydroxy-3-oxohexanoate, a key intermediate for the preparation of HMG-CoA reductase inhibitors (statins). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.037
• 作为产物：
  描述：

  苄基缩水甘油醚 在 sodium hydroxide 作用下， 以 dimethylformamide-purified water 为溶剂， 以52%的产率得到4-(benzyloxy)-3-hydroxybutanenitrile
  参考文献：
  名称：

  Pyrimidine derivatives

  摘要：

  嘧啶衍生物可用作胃肠促动力药物，其化学式表示为##STR1##其中X为O或NR.sup.5，Y为O、S或NR.sup.5，其中R.sup.5为氢原子、C.sub.1 -C.sub.6烷基或类似物；R.sup.1和R.sup.2可以相同也可以不同，每个都是氢原子、C.sub.1 -C.sub.6烷基或类似物；R.sup.3为CN，或COOR.sup.6，其中R.sup.6为C.sub.1 -C.sub.6烷基、C.sub.3 -C.sub.6环烷基、芳基或类似物；R.sup.4为--SR.sup.7或--NR.sup.8 R.sup.9，其中R.sup.7为C.sub.1 -C.sub.6烷基；R.sup.8为C.sub.1 -C.sub.6烷基或类似物；R.sup.9为氢原子、C.sub.1 -C.sub.6烷基或类似物，或R.sup.8和R.sup.9可以与它们连接的氮原子一起表示为化学式(X)的N-取代哌嗪环，其中R.sup.10代表C.sub.1 -C.sub.6烷基或类似物，或其药理学上可接受的盐。上述化合物可用作治疗消化道疾病的胃肠促动力药物。

  公开号：

  US05736550A1

文献信息

• Pyrimidine derivatives
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US05736550A1

  公开（公告）日：1998-04-07

  Pyrimidine derivatives useful as a gastrointestinal prokinetic agent, represented by formula ##STR1## wherein X is O or NR.sup.5, Y is O, S or NR.sup.5 wherein R.sup.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or the like; R.sup.1 and R.sup.2 may be the same or different and each is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or the like; R.sup.3 is CN, or COOR.sup.6 wherein R.sup.6 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, an aryl group or the like; R.sup.4 is --SR.sup.7 or --NR.sup.8 R.sup.9 wherein R.sup.7 is a C.sub.1 -C.sub.6 alkyl group; R.sup.8 is a C.sub.1 -C.sub.6 alkyl group or the like; R.sup.9 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or the like, or R.sup.8 and R.sup.9 may represent, together with the nitrogen atom to which they are attached, an N-substituted piperazine ring of formula (X) ##STR2## wherein R.sup.10 represents a C.sub.1 -C.sub.6 alkyl group or the like or a pharmacologically acceptable salt thereof. The above-mentioned compounds are useful as a gastrointestinal prokinetic agent used for the therapy of digestive tract diseases.

  嘧啶衍生物可用作胃肠促动力药物，其化学式表示为##STR1##其中X为O或NR.sup.5，Y为O、S或NR.sup.5，其中R.sup.5为氢原子、C.sub.1 -C.sub.6烷基或类似物；R.sup.1和R.sup.2可以相同也可以不同，每个都是氢原子、C.sub.1 -C.sub.6烷基或类似物；R.sup.3为CN，或COOR.sup.6，其中R.sup.6为C.sub.1 -C.sub.6烷基、C.sub.3 -C.sub.6环烷基、芳基或类似物；R.sup.4为--SR.sup.7或--NR.sup.8 R.sup.9，其中R.sup.7为C.sub.1 -C.sub.6烷基；R.sup.8为C.sub.1 -C.sub.6烷基或类似物；R.sup.9为氢原子、C.sub.1 -C.sub.6烷基或类似物，或R.sup.8和R.sup.9可以与它们连接的氮原子一起表示为化学式(X)的N-取代哌嗪环，其中R.sup.10代表C.sub.1 -C.sub.6烷基或类似物，或其药理学上可接受的盐。上述化合物可用作治疗消化道疾病的胃肠促动力药物。
• [EN] MORPHOLINE AND 1,4-OXAZEPANE AMIDES AS SOMATOSTATIN RECEPTOR SUBTYPE 4 (SSTR4) AGONISTS<br/>[FR] AMIDES DE MORPHOLINE ET DE 1,4-OXAZÉPANE UTILISÉS EN TANT QU'AGONISTES DU SOUS-TYPE 4 DU RÉCEPTEUR DE LA SOMATOSTATINE (SSTR4)
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2016075240A1

  公开（公告）日：2016-05-19

  The invention relates to morpholine and 1,4-oxazepane amide derivatives of general formula (I), which are agonists of somatostatin receptor subtype 4 (SSTR4), useful for preventing or treating medical disorders related to SSTR4. In addition, the invention relates to processes for preparing pharmaceutical compositions as well as processes for manufacture of the compounds according to the invention.

  这项发明涉及一般式(I)的吗啡啶和1,4-噁唑烷酮酰胺衍生物，它们是生长抑素受体亚型4（SSTR4）的激动剂，用于预防或治疗与SSTR4相关的医学疾病。此外，该发明涉及制备药物组合物的方法，以及根据该发明制造化合物的方法。
• Selective Monoalkylation of Acyclic Diols by Means of Dibutyltin Oxide and Fluoride Salts.
  作者：Nobuo NAGASHIMA、Masaji OHNO

  DOI：10.1248/cpb.39.1972

  日期：——

  Fluoride anion was found to promote monoalkylation reaction of diols by the stannylene acetal method, and selective monoalkylation of various acyclic diols was accomplished in good yields under mild conditions by employing this new method. Functional groups such as carboxylic acid ester, carboxamide, carbamate, nitrile, alkyl chloride, and ether were not affected under the reaction conditions.

  氟化物阴离子被发现能够通过锡烯醇反应促进二醇的单烷基化反应，并且在温和条件下，采用这种新方法成功实现了多种非环状二醇的选择性单烷基化，产率良好。在反应条件下，羧酸酯、羧酰胺、氨基甲酸酯、腈、烷基氯和醚等官能团没有受到影响。
• [EN] A NOVEL, GREEN AND COST EFFECTIVE PROCESS FOR SYNTHESIS OF TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDENE-HEXANOATE<br/>[FR] NOUVEAU PROCÉDÉ ÉCOLOGIQUE ET ÉCONOMIQUE POUR LA SYNTHÈSE DE TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDÈNE-HEXANOATE
  申请人：LUPIN LTD

  公开号：WO2014203045A1

  公开（公告）日：2014-12-24

  The present invention provides a process of preparation of an intermediate useful for the preparation of statins more particularly the present invention relates to an eco-friendly and cost effective process for the preparation of tert -butyl (3R,5S)-6-oxo-3,5-dihydroxy- 3,5-O-isopropylidene-hexanoate [I].

  本发明提供了一种制备中间体的过程，该中间体用于制备他汀类药物，更具体地说，本发明涉及一种环保且具有成本效益的过程，用于制备叔丁基(3R,5S)-6-氧化-3,5-二羟基-3,5- O-异丙基亚戊酸酯[I]。
• [EN] SPIROCYCLIC MDM2 MODULATOR AND USES THEREOF<br/>[FR] MODULATEUR SPIROCYCLIQUE DE MDM2 ET SES UTILISATIONS
  申请人：NEWAVE PHARMACEUTICAL INC

  公开号：WO2022159644A1

  公开（公告）日：2022-07-28

  The disclosure includes compounds of Formula (I), wherein each of Z, R0, R1, R2, R3, R4, R5, R6, R, L1, L2, L3, L4, L5, L6, Q1, Q2, W, m, n, r, and s, are defined herein. Also disclosed is a method for treating a neoplastic disease, autoimmune disease, and inflammatory disorder with these compounds.

  该披露涉及式(I)的化合物，其中Z、R0、R1、R2、R3、R4、R5、R6、R、L1、L2、L3、L4、L5、L6、Q1、Q2、W、m、n、r和s在此定义。还披露了使用这些化合物治疗肿瘤性疾病、自身免疫性疾病和炎症性疾病的方法。