(10E)-13-bromo-2,6,10-trimethyltrideca-2,6,10-triene | 140176-36-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (10E)-13-bromo-2,6,10-trimethyltrideca-2,6,10-triene
• 英文别名: homofarnesyl bromide；(6E,10E)-13-bromo-2,6,10-trimethyl-trideca-2,6,10-triene；13-bromo-2,6,10-trimethyl-trideca-2,6t,10t-triene；13-Brom-2,6,10-trimethyl-trideca-2,6t,10t-trien；13-Brom-2,6,10-trimethyl-tridecatrien-(2,6,10)；trans,trans-homofarnesyl bromide；13-Bromo-2,6,10-trimethyltrideca-2,6,10-triene；(6E,10E)-13-bromo-2,6,10-trimethyltrideca-2,6,10-triene
• CAS: 140176-36-9
• 化学式: C₁₆H₂₇Br
• 分子量: 299.294
• InChiKey: ZISCCZFUFBCDOO-NCZFFCEISA-N

物化性质

• 沸点：
  350.6±21.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (10E)-13-bromo-2,6,10-trimethyltrideca-2,6,10-triene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以94%的产率得到(E,E)-4,8,12-Trimethyl-3,7,11-tridecatrien-1-yl iodide
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.

  摘要：

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.

  DOI：

  10.1021/jo00036a008
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 氢溴酸 作用下， 生成 (10E)-13-bromo-2,6,10-trimethyltrideca-2,6,10-triene
  参考文献：
  名称：

  Julia et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 148, p. 820

  摘要：

  DOI：

文献信息

• Schizostatin, a potent squalene synthase inhibitor from Schizophyllum commune: Isolation, structure elucidation, and total synthesis
  作者：Tatsuo Tanimoto、Yoshio Tsujita、Kiyoshi Hamano、Hideyuki Haruyama、Takeshi Kinoshita、Tsuyoshi Hosoya、Satoru Kaneko、Keiko Tago、Hiroshi Kogen

  DOI：10.1016/0040-4039(95)01265-j

  日期：1995.8

  The novel schizostatin (1) has been isolated as a potent inhibitor of squalene synthase. Its structure elucidation and total synthesis are described. Synthesis of the Z-isomer 12 and its biological activity are also reported.

  已经分离出新型的schizostatin（1）作为角鲨烯合酶的有效抑制剂。描述了其结构阐明和全合成。还报道了Z-异构体12的合成及其生物学活性。
• Hydroxamic Acid-Based Bisubstrate Analog Inhibitors of Ras Farnesyl Protein Transferase
  作者：Dinesh V. Patel、Marian G. Young、Simon P. Robinson、Lisa Hunihan、Brenda J. Dean、Eric M. Gordon

  DOI：10.1021/jm960190h

  日期：1996.1.1

  microM), a bisubstrate analog involving anchorage of farnesyl and tripeptide groups by a hydroxamic acid-embedded linker. Starting from 16, a 1 order of magnitude improvement in in vitro potency was obtained by optimization of the linker (20, I50 = 4.35 microM). An additional 13-fold enhancement was achieved by substituting the tripeptide moiety VLS in 20 by VVM (23, I50 = 0.33 microM). The dependence of

  描述了新颖的，基于异羟肟酸的法呢基蛋白转移酶（FPT）的集体双底物类似物抑制剂的合理设计，合成和活性。这类化合物在结构上与常规FPT抑制剂不同，它们是非巯基的，并且是基于双底物的，而不是肽或FPP衍生的抑制剂。N-甲基异羟肟酸取代四肽CVLS（I50 = 1 microM）的巯基具有有害作用（10，I50> 360 microM），而双底物类似物16（I50 = 42.5 microM）实现了中等抑制作用。涉及通过异羟肟酸嵌入的接头锚定法呢基和三肽基团。从16开始，通过优化接头（20，I50 = 4.35 microM）获得了1个数量级的体外效价提高。通过用VVM取代20中的三肽部分VLS，可实现13倍的额外增强（23，I50 = 0.33 microM）。这些抑制剂对它们的肽和法呢基亚基的依赖性暗示了它们的双底物性质。与最初的铅16 [I50 = 42.5 microM]相比，化合物23（I50
• [EN] PREPARATION OF HOMOALLYLIC COMPOUNDS BY REACTION OF CYCLOPROPYLVINYL PRECURSORS WITH BRONSTEDT ACIDS<br/>[FR] PRÉPARATION DE COMPOSÉS HOMOALLYLIQUES PAR RÉACTION DE PRÉCURSEURS CYCLOPROPYLVINYLIQUES AVEC DES ACIDES DE BRÖNSTED
  申请人：GIVAUDAN SA

  公开号：WO2015059293A1

  公开（公告）日：2015-04-30

  A method of forming homoallylic compounds 2 from cyclopropylvinyl precursors 1 in the presence of a Bronsted acid HQ.

  在Bronsted酸HQ的存在下，从环丙基乙烯前体1形成同型烯丙基化合物2的方法。
• Schizostatin, a Novel Squalene Synthase Inhibitor Produced by the Mushroom, Schizophylllum commune. II. Structure Elucidation and Total Synthesis.
  作者：HIROSHI KOGEN、KEIKO TAGO、SATORU KANEKO、KIYOSHI HAMANO、KAORI ONODERA、HIDEYUKI HARUYAMA、KATSUHIRO MINAGAWA、TAKESHI KINOSHITA、TOMIO ISHIKAWA、TATSUO TANIMOTO、YOSHIO TSUJITA

  DOI：10.7164/antibiotics.49.624

  日期：——

  Schizostatin (1) has been isolated as a potent and selective inhibitor of squalene synthase. Its structure has been determined using spectroscopic methods: the compound is shown to be a diterpenoid which has a trans-dicarboxylic acid moiety. Total synthesis of schizostatin (1) was achieved by the highly regio- and stereoselective coupling reaction of an allylic bromide with a barium reagent. The Z-isomer

  Schizostatin（1）已被分离为角鲨烯合酶的有效和选择性抑制剂。它的结构已使用光谱法确定：该化合物显示为具有反式二羧酸部分的二萜类化合物。通过烯丙基溴与钡试剂的高度区域选择性和立体选择性偶合反应，可实现schizostatin（1）的全合成。Z-异构体16也使用有机铜试剂向乙炔二羧酸酯的立体选择性顺式加成制备。
• PREPARATION OF HOMOALLYLIC COMPOUNDS BY REACTION OF CYCLOPROPYLVINYL PRECURSORS WITH BRONSTEDT ACIDS
  申请人：GIVAUDANSA

  公开号：US20160251298A1

  公开（公告）日：2016-09-01

  A method of forming homoallylic compounds 2 from cyclopropylvinyl precursors 1 in the presence of a Bronsted acid HQ

  在Brønsted酸HQ存在下，使用环丙基乙烯基前体1形成同型烯丙基化合物2的方法。