(Z)-hex-3-ene-1-thiol | 89222-70-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: (Z)-hex-3-ene-1-thiol
• CAS: 89222-70-8
• 化学式: C₆H₁₂S
• 分子量: 116.227
• InChiKey: ROLNNHGYLSXDRV-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-hex-3-ene-1-thiol 在 lithium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.75h， 生成 <1S-<1α,2α(Z),3α(Z),4α>>-7-<3-<(3-Hexenylthio)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).

  DOI：

  10.1021/jm00125a009

文献信息

• A Systematic Study of Unsaturation in Lipid Nanoparticles Leads to Improved mRNA Transfection In Vivo
  作者：Sang M. Lee、Qiang Cheng、Xueliang Yu、Shuai Liu、Lindsay T. Johnson、Daniel J. Siegwart

  DOI：10.1002/anie.202013927

  日期：2021.3.8

  ionizable lipid series (4A3) emerged from in vitro and in vivo screening, where the 4A3 core with a citronellol‐based (Cit) periphery emerged as best. We studied the interaction between LNPs and a model endosomal membrane where 4A3‐Cit demonstrated superior lipid fusion over saturated lipids, suggesting its unsaturated tail promotes endosomal escape. Furthermore, 4A3‐Cit significantly improved mRNA delivery

  脂质纳米粒子 (LNP) 代表了 mRNA 递送的领先概念。不饱和脂质在自然界中发挥着重要作用，具有 mRNA 治疗的潜力，但很难通过化学合成获得。为了系统地研究不饱和度的作用，利用模块化反应来访问由不饱和硫醇合成实现的 91 种氨基脂质库。经过体外和体内筛选，出现了可电离脂质系列 (4A3)，其中具有香茅醇基 (Cit) 外周的 4A3 核心表现最佳。我们研究了 LNP 和模型内体膜之间的相互作用，其中 4A3-Cit 表现出优于饱和脂质的脂质融合，表明其不饱和尾部促进内体逃逸。此外，4A3-Cit 通过选择性器官靶向 (SORT) 显着提高了体内 mRNA 递送效率，导致蛋白表达比亲本 LNP 增加了 18 倍。这些发现深入了解脂质不饱和如何促进 mRNA 递送，并证明脂质混合如何增强功效。
• 7-Oxabicycloheptane substituted thio prostaglandin analogs
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0164075A2

  公开（公告）日：1985-12-11

  7-Oxabicycloheptane substituted thio prostaglandin analogs are provided having the structural formula wherein p is 0 to 4; A is CH=CH, (CH2)2, or a single bond; m is 0 to 8; R is H, lower alkyl, alkali metal or tris(hydroxymethyl)-aminomethane; n is 1 to 4; n' is 0, 1 or 2; q is 1 to 12; X is wherein R2 and R3 may be the same or different and are H or lower alkyl; t is 0 to 5; and R1 is H, lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl, and including all stereoisomers thereof. The compounds are cardiovascular agents and antiinflammatory agents useful, for example, in the treatment of thrombolytic disease, inflammation and pain.

  7-氧杂双环庚烷取代的硫代前列腺素类似物的结构式为 其中 p 是 0 至 4；A 是 CH=CH、(CH2)2 或单键；m 是 0 至 8；R 是 H、低级烷基、碱金属或三(羟甲基)氨基甲烷；n 是 1 至 4；n'是 0、1 或 2；q 是 1 至 12；X 是 其中 R2 和 R3 可以相同或不同，并且是 H 或低级烷基；t 是 0 至 5；R1 是 H、低级烷基、芳基、芳烷基、环烷基或环烷基烷基，包括其所有立体异构体。 这些化合物是心血管药剂和抗炎药剂，可用于治疗血栓溶解疾病、炎症和疼痛等。
• Ink composition, inkjet recording method, printed material, process for producing lithographic printing plate, and lithographic printing plate
  申请人：Fujifilm Corporation

  公开号：EP1808466A1

  公开（公告）日：2007-07-18

  An ink composition is provided that includes (A) an acid-generating compound having an anion represented by any one of Formulae (I) to (XI), (B) a cationacally polymerizable compound, and (C) a colorant. (In the formulae, R1 to R3 independently denote a monovalent organic group, Rb1 to Rb3, Rf1, and Rf2 independently denote a perfluoroalkyl group, a perfluoroaryl group, or an aryl group substituted with at least one fluorine atom or perfluoroalkyl group, X1 to X3 independently denote a monovalent organic group, and Y1 denotes a hydrogen atom or a monovalent organic group.)

  提供了一种油墨组合物，其中包括 (A) 具有由式 (I) 至 (XI) 中任一个阴离子代表的酸生成化合物，(B) 阳离子可聚合化合物，以及 (C) 着色剂。 (在式中，R1 至 R3 独立地表示一价有机基团，Rb1 至 Rb3、Rf1 和 Rf2 独立地表示全氟烷基、全氟芳基或被至少一个氟原子或全氟烷基取代的芳基，X1 至 X3 独立地表示一价有机基团，Y1 表示氢原子或一价有机基团)。
• THIOETHER PRECURSORS FOR FRAGRANT KETONES AND ALDEHYDES
  申请人：Givaudan SA

  公开号：EP3533786A1

  公开（公告）日：2019-09-04

  Disclosed is a use of a compound of formula (I), a composition of matter comprising a compound of formula (I) and a fragrance ingredient comprising a compound of formula (I).

  公开了一种式 (I) 化合物的用途、一种包含式 (I) 化合物的物质组合物和一种包含式 (I) 化合物的香料成分。
• Thioether precursors for fragrant ketones and aldehydes
  申请人：GIVAUDAN SA

  公开号：US11359161B2

  公开（公告）日：2022-06-14

  Disclosed is a use of a compound of formula (I), a composition of matter comprising a compound of formula (I) and a consumer product comprising a compound of formula (I).

  公开了一种式 (I) 化合物的用途、一种包含式 (I) 化合物的物质组合物和一种包含式 (I) 化合物的消费品。