methyl (Z)-7-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-7-pyridin-3-ylhept-6-enoate | 213620-92-9

• 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: methyl (Z)-7-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-7-pyridin-3-ylhept-6-enoate
• CAS: 213620-92-9
• 化学式: C₂₆H₃₇NO₃Si
• 分子量: 439.67
• InChiKey: AABIEIPYULXEPX-IWIPYMOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (Z)-7-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-7-pyridin-3-ylhept-6-enoate 在 jones reagent 作用下， 以 丙酮 为溶剂， 生成 3-[(Z)-7-methoxy-7-oxo-1-pyridin-3-ylhept-1-enyl]benzoic acid
  参考文献：
  名称：

  Development of dual-acting agents for thromboxane receptor antagonism and thromboxane synthase inhibition. 2. Design, synthesis, and evaluation of a novel series of phenyl oxazole derivatives

  摘要：

  Synthesis and initial in vitro evaluation of a novel series of phenyl oxazole derivatives are described. An SAR study of the novel dual-acting TRA/TSI agent has revealed that the lipophilicity of the oxazole amide substituents greatly influences the TRA activity but not the TSI. The chain length of the alkenoic acid side chain affects both TRA and TSI. The optimal chain length for the combined activities was found to be n = 4 (heptenoic acid). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00353-9
• 作为产物：
  描述：

  1,3-苯二甲醇 在 咪唑 、 manganese(IV) oxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 methyl (Z)-7-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-7-pyridin-3-ylhept-6-enoate
  参考文献：
  名称：

  Development of dual-acting agents for thromboxane receptor antagonism and thromboxane synthase inhibition. 2. Design, synthesis, and evaluation of a novel series of phenyl oxazole derivatives

  摘要：

  Synthesis and initial in vitro evaluation of a novel series of phenyl oxazole derivatives are described. An SAR study of the novel dual-acting TRA/TSI agent has revealed that the lipophilicity of the oxazole amide substituents greatly influences the TRA activity but not the TSI. The chain length of the alkenoic acid side chain affects both TRA and TSI. The optimal chain length for the combined activities was found to be n = 4 (heptenoic acid). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00353-9

文献信息

• Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry
  作者：Kumiko Takeuchi、Jonathan W. Paschal、Richard J. Loncharich

  DOI：10.1021/jo00106a029

  日期：1995.1

  Investigation of the stereoselectivity observed in the Wittig reaction of aromatic ketones with ''nonstabilized'' phosphonium ylides revealed that the nature of the substituent on the phenyl ring of phenyl S-pyridyl ketone determined the stereoselectivity. Generally the Wittig reaction of such ketones with carboxy phosphonium ylides proceeded preferentially to yield (Z)-olefin, albeit with modest selectivity. However, the reaction with aryl sulfonamido-substituted aromatic ketones resulted in high (E)-stereoselectivity. In order to understand the origin of this high (E)-selectivity, a semiempirical conformational analysis of the four uncharged diastereomeric oxaphosphetane intermediates was performed with a cumulatively modified sampling procedure to generate initial conformations, followed by full energy optimization. Computational studies of the unsubstituted and 4-nitrophenyl-substituted oxaphosphetane intermediates were consistent with the low (Z)stereoselectivity observed. The results in the calculations of the aryl sulfonamido-substituted intermediate likewise were consistent with the high (E)-stereoselectivity observed. Calculations of the potassium-coordinated acid anion of the latter species were also performed. All calculations supported interaction of the sulfonamido and carboxylate groups by either hydrogen bonding or salt bridge formation which appears to effect the final stereochemical outcome. Furthermore, we investigated the stereoselectivity of Wittig reactions in which the sulfonamido NH or the carboxylate were removed. In both cases, the (Z)-olefin was formed preferentially, thereby supporting the existence of intramolecular hydrogen bonding or salt bridge formation.
• Development of dual-acting agents for thromboxane receptor antagonism and thromboxane synthase inhibition. 2. Design, synthesis, and evaluation of a novel series of phenyl oxazole derivatives
  作者：Kumiko Takeuchi、Todd J Kohn、Dale E Mais、Timothy A True、Virginia L Wyss、Joseph A Jakubowski

  DOI：10.1016/s0960-894x(98)00353-9

  日期：1998.8

  Synthesis and initial in vitro evaluation of a novel series of phenyl oxazole derivatives are described. An SAR study of the novel dual-acting TRA/TSI agent has revealed that the lipophilicity of the oxazole amide substituents greatly influences the TRA activity but not the TSI. The chain length of the alkenoic acid side chain affects both TRA and TSI. The optimal chain length for the combined activities was found to be n = 4 (heptenoic acid). (C) 1998 Elsevier Science Ltd. All rights reserved.