(2R)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate | 851372-04-8

• 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: (2R)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate
• 英文别名: [(2R)-2-hydroxy-4-phenylbutyl] 4-methylbenzenesulfonate
• CAS: 851372-04-8
• 化学式: C₁₇H₂₀O₄S
• 分子量: 320.409
• InChiKey: MPSYBFGRIDGDMF-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 在 copper(l) iodide 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.17h， 生成
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors

  摘要：

  A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized anti evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.

  DOI：

  10.1021/jm980162u
• 作为产物：
  描述：

  三苯基苄基溴化膦 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 氢气 、 sodium 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 正己烷 为溶剂， 反应 26.33h， 生成 (2R)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  以声化学 Blaise 反应为关键步骤的 (+)- 和 (-)-Dihydrokavain 全合成

  摘要：

  以 2,3-O-异亚丙基-D-甘油醛 (2) 作为手性材料，以声化学 Blaise 反应为关键步骤合成天然存在的 (S)-(+)-dihydrokavain (1a) . (S)-(+)-dihydrokavain (1a) 的绝对构型首次通过手性来源的全合成得到证明。其相反的对映异构体 (R)-(-)-dihydrokavain (1b) 也是在 Mitsunobu 反应中手性中心反转后合成的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200400833

文献信息

• Highly stereoselective Friedel–Crafts alkylations of unactivated benzenes by episulfonium ion cyclizations
  作者：Bruce P Branchaud、Heather S Blanchette

  DOI：10.1016/s0040-4039(01)02173-6

  日期：2002.1

  Intermolecular additions of highly enantiomerically enriched episulfonium ions onto activated benzene rings are known to accomplish chiral Friedel–Crafts alkylations. Unactivated benzenes are either unreactive or can give low stereoselectivities. Intramolecular cyclizations should be faster than intermolecular additions; thus, cyclization reactions should be able to avoid undesired episulfonium ion

  在活性苯环上分子间添加高度对映体富集的epi硫离子可完成手性Friedel-Crafts烷基化反应。未活化的苯要么不反应，要么会降低立体选择性。分子内环化应比分子间加成更快。因此，环化反应应能够避免不希望的epi硫离子外消旋作用。此处报道的工作证明了这一假设，并证明了对映体富集的epi磺酸盐在未活化的苯环上的环化反应具有很高的立体选择性。
• Total Synthesis of a Mevinic Acid Analog
  作者：Thummalapally Srikanth Reddy、Dorigondla Kumar Reddy、Manchala Narasimhulu、Dasari Ramesh、Yenamandra Venkateswarlu

  DOI：10.1002/hlca.201000062

  日期：2010.11

  Total synthesis of mevinic acid analog 1 has been achieved efficiently starting from chiral 2,3‐O‐isopropylidene‐D‐glyceraldehyde (2). The synthesis involves Mitsunobu reaction and Evans' intramolecular oxa‐Michael syn‐addition reactions as key steps.

  从手性2,3- O-异亚丙基-D-甘油醛（2）开始已成功实现了全酸类似物1的全合成。合成涉及Mitsunobu反应和Evans的分子内oxa- Michael合成加成反应作为关键步骤。
• PROCESS FOR PREPARATION OF 13,14-DIHYDRO-PGF2 ALPHA DERIVATIVES
  申请人：MARTYNOW Jacek

  公开号：US20080207926A1

  公开（公告）日：2008-08-28

  The invention relates to a process for the preparation of 13,14-dihydro-PGF 2α derivatives of R or S configuration at carbon 15, represented by the general formula (I), wherein the identity of the substituents is defined in the description. Compounds of the formula (I) are valuable biologically-active substances or intermediates in the preparation thereof. The invention especially relates to the process for preparation of 13,14-dihydro-15(R)-17-substituted-18,19,20-trinor-PGF 2α , i.e., latanoprost.

  本发明涉及一种制备在碳15处具有R或S构型的13,14-二氢-PGF2α衍生物的方法，该衍生物由通式（I）表示，其中置换基的身份在说明中定义。式（I）化合物是有价值的生物活性物质或制备中间体。本发明特别涉及制备13,14-二氢-15（R）-17-取代-18,19,20-三去甲-PGF2α，即拉坦前列素的方法。
• WO2006/112742
  申请人：——

  公开号：——

  公开（公告）日：——
• US7897793B2
  申请人：——

  公开号：US7897793B2

  公开（公告）日：2011-03-01