2-mercaptoethyl pivalate | 190062-33-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-mercaptoethyl pivalate
• 英文别名: 2-Sulfanylethyl 2,2-dimethylpropanoate
• CAS: 190062-33-0
• 化学式: C₇H₁₄O₂S
• 分子量: 162.253
• InChiKey: TWGNDLTWVYZRPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-mercaptoethyl pivalate 在 四氮唑 、 叔丁基过氧化氢 作用下， 生成 tBu(iso)SATE d4T
  参考文献：
  名称：

  The Pronucleotide Approach. I. Synthesis, Anti-HIV Activity and Preliminary Stability Studies of MononucleosideS,S′-Bis(O-acyl-2-oxyethyl) Phosphorodithiolates

  摘要：

  The synthesis, in vitro anti-HIV activity, and preliminary stability studies of several mononucleoside phosphorodithiolate derivatives incorporating a new kind of biolabile phosphate-protection, namely O-pivaloyl-2-oxyethyl, are reported. Our preliminary results strongly support the hypothesis that such pronucleotides exert their biological effects via intracellular delivery of the corresponding 5'-mononucleotide.

  DOI：

  10.1080/07328319708006180
• 作为产物：
  描述：

  di(2-pivaloyloxyethyl)disulfide 在 Rh(H)(PEt₃)₃ 氢气 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以92%的产率得到2-mercaptoethyl pivalate
  参考文献：
  名称：

  铑配合物催化的氢和氧氧化/还原硫醇和二硫化物的相互转化

  摘要：

  RhH（PPh 3）4催化氢将二硫化物还原为硫醇，而RhH（PPh 3）4 / 1,4-双（二苯基膦基）丁烷（dppb）则催化氧将硫醇氧化为二硫化物。

  DOI：

  10.1016/j.tetlet.2005.06.169

文献信息

• Mononucleoside phosphorodithiolates as mononucleotide prodrugs
  作者：Nathalie Schlienger、Isabelle Lefebvre、Anne-Marie Aubertin、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1016/j.ejmech.2021.113914

  日期：2022.1

  The synthesis and in vitro anti-HIV activity of a novel series of pronucleotides are reported. These prodrugs were characterized by a phosphorodithiolate structure, incorporating two O-pivaloyl-2-oxyethyl substituents as biolabile phosphate protections. The compounds were obtained following an original one-pot three-step procedure, involving the formation of a phosphorodithioite intermediate which

  报道了一系列新型原核苷酸的合成和体外抗 HIV 活性。这些前药的特征在于二硫代磷酸酯结构，结合了两个O -pivaloyl-2-oxyethyl 取代基作为生物不稳定的磷酸盐保护。这些化合物是按照原始的一锅三步程序获得的，包括形成原位氧化的二硫代磷酸酯中间体。在体外，比较抗 HIV 评估表明，这种原始前药能够使相应的 5'-单核苷酸在细胞内有效释放。2',3'-双脱氧腺苷 (ddA) 3的前核苷酸在各种细胞系中表现出非常有效的抗逆转录病毒作用，在纳摩尔浓度范围内具有 50% 的有效浓度 (EC 50 ) 值。在原代单核细胞/巨噬细胞中，该衍生物抑制 HIV 复制的效力 (EC 50 0.23 pM) 是 ddA 的500 倍，前药的选择性指数是母体核苷的 50 倍。
• Generation of Alkyl Radicals from Thiols via Zinc Thiolates: Application for the Synthesis of <i>gem</i> ‐Difluorostyrenes
  作者：Vyacheslav I. Supranovich、Vitalij V. Levin、Vladimir A. Kokorekin、Alexander D. Dilman

  DOI：10.1002/adsc.202100088

  日期：2021.6.8

  Reaction of thiols with α-(trifluoromethyl)styrenes under photocatalytic conditions leading to desulfurative allylic fluorine substitution is described. The reaction is performed by treatment of thiols with benzyl zinc chloride to generate zinc thiolates followed by visible light induced desulfurization by means of triphenylphosphine. Radicals formed after the C−S bond cleavage react with the double

  描述了硫醇与 α-（三氟甲基）苯乙烯在光催化条件下的反应，导致脱硫烯丙基氟取代。该反应通过用苄基氯化锌处理硫醇生成硫醇锌，然后借助三苯基膦进行可见光诱导脱硫来进行。在 C-S 键断裂后形成的自由基与双键反应，得到gem-二氟苯乙烯。
• 2' ,5' -Oligoadenylate analogs
  申请人：Koizumi Makoto

  公开号：US20050261235A1

  公开（公告）日：2005-11-24

  A 2-5A analog represented by the formula (1): wherein m is 0 or 1; n is 0 to 2; R 1 represents an alkoxy group having from 1 to 6 carbon atoms which may be substituted, an unprotected mercapto group, a mercapto group protected by a nucleic acid synthesis protecting group, or an alkylthio group having from 1 to 4 carbon atoms which may be substituted; R 2 , R 3 , R 4 , R 5 and R 6 represent an unprotected hydroxyl group, a hydroxyl group protected by a nucleic acid synthesis protecting group, an alkoxy group having from 1 to 6 carbon atoms which may be substituted, an unprotected mercapto group, a mercapto group protected by a nucleic acid synthesis protecting group, or an alkylthio group having from 1 to 4 carbon atoms which may be substituted; R 7 represents an oxygen atom, or a —O(CH 2 CH 2 O)q-group, wherein q is 2 to 6; R 8 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms which may be substituted, or a 5′-phosphorylated oligonucleotide analog which has one hydroxyl group removed from the 5′-phosphoric acid group; E 1 , E 2 , E 3 and E 4 represent a naturally occurring or modified nucleic acid unit, or a pharmacologically acceptable salt thereof.

  一种由公式（1）表示的2-5A模拟物，其中m为0或1；n为0至2；R1表示具有1至6个碳原子的烷氧基，可以被取代，未保护的巯基，通过核酸合成保护基保护的巯基，或者具有1至4个碳原子的烷硫基，可以被取代；R2、R3、R4、R5和R6表示未保护的羟基，通过核酸合成保护基保护的羟基，具有1至6个碳原子的烷氧基，可以被取代，未保护的巯基，通过核酸合成保护基保护的巯基，或者具有1至4个碳原子的烷硫基，可以被取代；R7表示氧原子，或者-O(CH2CH2O)q-基团，其中q为2至6；R8表示氢原子，具有1至6个碳原子的烷基，可以被取代，或者从5'-磷酸基团中去除一个羟基的5'-磷酸寡核苷酸类似物；E1、E2、E3和E4表示天然或修饰的核酸单元，或其药理学上可接受的盐。
• Stabilizers for halogen-containing polymers
  申请人：MORTON INTERNATIONAL, INC.

  公开号：EP0254392A2

  公开（公告）日：1988-01-27

  A stabilizing composition for halogen-containing polymers, comprising a diorganotin oxide compound such as dibutyl or dioctyl tin oxide, an ethylenically unsaturated dicarboxylic acid ester compound such as dibutyl or dioctyl maleate and a mercaptan-containing organic compound such as isooctyl mercaptopropionate.

  一种用于含卤聚合物的稳定组合物，包括二甘醇锡氧化物化合物（如二丁基或二 辛基氧化锡）、乙烯不饱和二羧酸酯化合物（如马来酸二丁酯或马来酸二辛 酯）和含硫醇的有机化合物（如巯基丙酸异辛酯）。
• Improved PVC foam compositions
  申请人：MORTON INTERNATIONAL, INC.

  公开号：EP0850987A1

  公开（公告）日：1998-07-01

  The density of rigid foamed articles made by the thermal decomposition of a blowing agent in a vinyl chloride polymer is reduced by the use of an organotin mercaptoalkylcarboxylate, alone, or in combination with an organotin halide or carboxylate which activate the blowing agent. Sulfides made from said organotin mercaptoalkylcarboxylate are also superior activators of the blowing agent.

  单独使用有机锡巯基烷基羧酸盐，或与有机锡卤化物或羧酸盐结合使用，可激活发泡剂，从而降低通过发泡剂在氯乙烯聚合物中的热分解制成的硬质发泡物品的密度。由上述有机锡巯基烷基羧酸酯制成的硫化物也是发泡剂的优质活化剂。