(-)-(R)-6-Methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester | 156661-61-9

• 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: (-)-(R)-6-Methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester
• 英文别名: (6R,4E)-ethyl 6-methyl-9-phenylnon-4-enoate；ethyl (E,6R)-6-methyl-9-phenylnon-4-enoate
• CAS: 156661-61-9
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: KUUOZEANWRWVQW-JCVNQNCUSA-N

物化性质

• 沸点：
  374.3±31.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(R)-6-Methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 (+)-zaragozic acid
  参考文献：
  名称：

  (+)-Zaragozic Acid C: Synthesis and Related Studies

  摘要：

  The asymmetric synthesis of the potent squalene synthase inhibitor (+)-zaragozic acid C is described. The synthesis allows for the preparation of multigram quantities of the dioxabicyclooctane core common to all members of this class of fungal metabolites. Supporting studies include (1) the use of [Cr(OAc)(2) . H2O](2) for the stereoselective reduction of ynones to trans enones, (2) an investigation of the diastereoselective dihydroxylation of gamma-alkoxy-alpha,beta-trans trans enones, and (3) nucleophilic addition of Me(3)SiC equivalent to CLi to a dioxabicyclooctanone, wherein the product diastereoselectivity is observed to vary as a function of cosolvents (tertiary amines) and additives (LiBr). In addition, an acylation protocol is reported which permits the regioselective installation of the C(6) O-acyl side chain.

  DOI：

  10.1021/ja00136a008
• 作为产物：
  描述：

  Cinnamyl bromide 在 palladium on activated charcoal 、 丙酸 lithium aluminium tetrahydride 、 草酰氯 、 氢气 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， -78.0~138.0 ℃ 、275.79 kPa 条件下， 反应 18.0h， 生成 (-)-(R)-6-Methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester
  参考文献：
  名称：

  Absolute Stereochemistry of the Squalene Synthase Inhibitor Zaragozic Acid C

  摘要：

  DOI：

  10.1021/jo00087a054

文献信息

• “One-Pot” Reductive Lactone Alkylation Provides a Concise Asymmetric Synthesis of Chiral Isoprenoid Targets
  作者：Jia Cao、Patrick Perlmutter

  DOI：10.1021/ol401801g

  日期：2013.9.6

  An efficient method, based on nucleophilic addition to lactones followed by modified in situ Clemmensen reduction, provides a short synthetic route to chiral isoprenoid targets. The efficacy of this method has been exemplified through the synthesis of several targets including the commercial fragrance Rosaphen, the side chain of Zaragozic acid C, the cotton leaf sex pheromone, and the side chains of

  一种有效的方法，基于向内酯的亲核加成，然后进行修饰的原位Clemmensen还原，为合成手性类异戊二烯靶标提供了一条简短的合成途径。该方法的功效已通过几种靶标的合成得到了证明，其中包括商业香料罗莎芬，扎拉果酸C的侧链，棉叶性信息素和维生素E的侧链。
• Inhibitors of squalene synthase and protein farnesyltransferase
  申请人：Abbott Laboratories

  公开号：US05831115A1

  公开（公告）日：1998-11-03

  The present invention provides a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof, which are useful for inhibiting protein farnesyltransferase and the farnesylation of the oncogene protein Ras or inhibiting de novo squalene production resulting in the inhibition of cholesterol biosynthesis, processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and to methods of using such compounds.

  本发明提供了式子##STR1##的化合物或其药学上可接受的盐，这些化合物对于抑制蛋白酰基转移酶和致癌基因蛋白Ras的酰化或抑制新生角鲨烷的产生从而抑制胆固醇生物合成是有用的。本发明还提供了制备这些化合物的方法及在这些方法中有用的中间体，一种制药组合物以及使用这些化合物的方法。
• Cyclobutane derivatives as inhibitors of protein farnesyltransferase
  申请人：ABBOTT LABORATORIES

  公开号：EP1090908A2

  公开（公告）日：2001-04-11

  The present invention provides a compound of formula (II) or a pharmaceutically acceptable salt thereof, which is useful for inhibiting protein farnesyltransferase and the farnesylation of the oncogene protein Ras, processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and to methods of using such compounds.

  本发明提供了一种可用于抑制蛋白法尼基转移酶和癌基因蛋白 Ras 的法尼基化的式 (II) 化合物或其药学上可接受的盐，还提供了制备本发明化合物的工艺以及在这些工艺中有用的中间体、药物组合物和使用这些化合物的方法。
• CYCLOBUTANE DERIVATIVES AS INHIBITORS OF SQUALENE SYNTHASE AND PROTEIN FARNESYLTRANSFERASE
  申请人：Abbott Laboratories

  公开号：EP0821665A1

  公开（公告）日：1998-02-04
• US5831115A
  申请人：——

  公开号：US5831115A

  公开（公告）日：1998-11-03