1,3-Bis<(phenylmethyl)thio>-2-propanone | 19216-97-8

• 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: 1,3-Bis<(phenylmethyl)thio>-2-propanone
• 英文别名: 1,3-bis-(benzylthio)propan-2-one；1,3-bis(benzylthio)-2-propanone；1,3-bis(benzylthio)acetone；1,3-di(benzylthio)acetone；1,3-bis-benzylsulfanyl-acetone；α.α'-Bis-benzylmercapto-aceton；2-Propanone, 1,3-bis[(phenylmethyl)thio]-；1,3-bis(benzylsulfanyl)propan-2-one
• CAS: 19216-97-8
• 化学式: C₁₇H₁₈OS₂
• 分子量: 302.461
• InChiKey: DZJUMBZKYYNLDX-UHFFFAOYSA-N

物化性质

• 沸点：
  430.3±40.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-Bis<(phenylmethyl)thio>-2-propanone 在 sodium hydroxide 、 permanganate(VII) ion 作用下， 生成 benzylsulfinic acid
  参考文献：
  名称：

  Fromm; Kapeller; Taubmann, Chemische Berichte, 1928, vol. 61, p. 1354

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二氯丙酮 、 苄硫醇 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以44%的产率得到1,3-Bis<(phenylmethyl)thio>-2-propanone
  参考文献：
  名称：

  1,2-DITHIOLANE AND DITHIOL COMPOUNDS USEFUL IN TREATING MUTANT EGFR-MEDIATED DISEASES AND CONDITIONS

  摘要：

  该发明的组合物包括1,2-二硫杂环烷、二硫醇和相关化合物，可用作治疗剂，用于治疗和预防与EGFR活性异常相关的疾病和病况。

  公开号：

  US20180208584A1

文献信息

• 1,2-dithiolane and dithiol compounds useful in treating mutant EGFR-mediated diseases and conditions
  申请人：Sabila Biosciences LLC

  公开号：US10246444B2

  公开（公告）日：2019-04-02

  Compositions of the invention comprise 1,2-dithiolane, dithiol and related compounds useful as therapeutic agents for the treatment and prevention of diseases and conditions associated with aberrant EGFR activity.

  本发明的组合物包括 1,2-二硫环戊烷、二硫醇及相关化合物，可作为治疗剂用于治疗和预防与表皮生长因子受体活性异常相关的疾病和病症。
• Uneme, Hideki; Mitsudera, Hiroyuki; Kamikado, Toshiya, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 12, p. 2023 - 2033
  作者：Uneme, Hideki、Mitsudera, Hiroyuki、Kamikado, Toshiya、Kono, Yoshiaki、Manabe, Yukiaki、Numata, Mitsuo

  DOI：——

  日期：——
• Povalyaeva, O.S.; Rodionov, V.Ya.; Suvorov, N.M., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 773 - 782
  作者：Povalyaeva, O.S.、Rodionov, V.Ya.、Suvorov, N.M.

  DOI：——

  日期：——
• Cyclic ketones via the reaction of dithiols with 1,3-dichloroacetone. An unexpected base-catalyzed rearrangement of .alpha.,.alpha.'-dithia ketones
  作者：Jer Jye Chiu、Rupinder S. Grewal、Harold Hart、Donald L. Ward

  DOI：10.1021/jo00058a042

  日期：1993.3

  The reaction of dithiols with 1,3-dichloroacetone under high dilution and catalyzed by cesium carbonate in DMF affords macrocyclic ketones in good yield. Examples of functionalized cyclophanes prepared in this way include 10, 15, 16, 19, 21, and 24. With NaOMe/MeOH as the base, dithiol 14 gave ring-contracted ketone 17 in low yield, in addition to the expected 15 and 16. Ketone 17 was the sole product, in good yield, from 14 and 1,1-dichloroacetone. NaOMe/MeOH also brought about the novel ring contraction of 10 to 11 and 11 to 12. X-ray structures of 10,12,16,19, and 21 are briefly described. Possible mechanisms for the formation of 17 from 14 and for the rearrangement of 10 --> 11 --> 12 are discussed.
• Nereistoxin and Cartap Neurotoxicity Attributable to Direct Block of the Insect Nicotinic Receptor/Channel
  作者：Seog-Jong Lee、Motohiro Tomizawa、John E. Casida

  DOI：10.1021/jf021149s

  日期：2003.4.1

  Nereistoxin (NTX) (4-dimethylamino-1,2-dithiolane) is the naturally occurring prototype for cartap [the bis(thiocarbamate) derivative of the NTX dithiol], which is generally regarded as a proinsecticide reverting to NTX. The aim of this study is to define the target site(s) for dithiolanes and dithiol esters. The affinity of [H-3]NTX was not suitable for binding assays with honeybee (Apis mellifera) head membranes. However, NTX and cartap are equally potent, direct-acting, and competitive displacers of [H-3]thienylcyclohexylpiperidine binding at the noncompetitive blocker (NCB) site of the Apis nicotinic acetylcholine receptor (nAChR)/channel. NTX also binds at the Apis [H-3]imidacloprid agonist site, but cartap does not. As candidate metabolic pathways, sequential N-desmethylation and S-oxidation of NTX progressively reduce its potency at the NCB site and toxicity to houseflies. A P450 inhibitor reduces the toxicity of NTX and enhances it with cartap. Surprisingly, cartap is not just a pro-NTX but instead directly induces inhibitory neurotoxicity by blocking the nAChR/channel, whereas NTX may have dual NCB and agonist targets.