allyl trityl sulphide | 29167-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: allyl trityl sulphide
• 英文别名: allyl trityl sulfide；trityl allyl sulfide；allyl tritylsulfide；Allyl-tritylsulfid；[diphenyl(prop-2-enylsulfanyl)methyl]benzene
• CAS: 29167-22-4
• 化学式: C₂₂H₂₀S
• 分子量: 316.467
• InChiKey: ZTJDYARJYLKTKR-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C
• 沸点：
  423.8±14.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  allyl trityl sulphide 在 [RuHCl(CO)(PPh₃)₃] 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以94%的产率得到trityl 1-propenyl sulfide
  参考文献：
  名称：

  通过烯丙基化合物的串联异构化为乙烯基衍生物和将腈类化合物的腈类化合物进行1,3-偶极环加成反应，方便地合成异恶唑啉

  摘要：

  通过将QCH（X）CHCH（Y）串联异构化为QC（X）CHCH 2（Y）（Q = RO，RS，R 2 N，R 3 Si等; X ＝ H，R，OR； Y ＝ H，R； R ＝烷基，芳基）被钌配合物催化，并且提出了后者化合物的1，3-偶极环加成成芳族腈氧化物。还描述了QCH（X）CHCH（Y）与2,6-二氯苄腈氧化物的环加成。讨论了氮氧化物与烯丙基和1-丙烯基（通常为乙烯基）化合物的环加成反应的区域选择性和立体选择性。

  DOI：

  10.1016/j.tetlet.2008.07.176
• 作为产物：
  描述：

  三苯基甲醇 、 烯丙硫醇 在 硫酸 作用下， 以 甲醇 、 溶剂黄146 、 苯 为溶剂， 生成 allyl trityl sulphide
  参考文献：
  名称：

  Novel (trans 1-propenyl)disulfide derivative and process for preparing

  摘要：

  具有杰出抗肿瘤效果的（反1-丙烯基）二硫化物衍生物，由以下一般式代表：##STR1##，其中R是较低的烷基烯基团，R'是氢原子或羧基保护基，通过允许羧酸硫醇衍生物，由以下一般式代表：AS--R--COOR'，其中R和R'具有上述定义的相同含义，A是可由卤化剂释放的硫醇保护基，与反1-丙烯硫醇衍生物反应制备，由以下一般式代表：##STR2##，其中A具有上述定义的相同含义，在卤化剂存在下。

  公开号：

  US05011975A1

文献信息

• Double bond migration in Sallyl systems catalysed by [RuClH(CO)(PPh3)3]
  作者：Nikodem Kuźnik、Stanisław Krompiec、Tadeusz Bieg、Stefan Baj、Krzysztof Skutil、Anna Chrobok

  DOI：10.1016/s0022-328x(02)02111-3

  日期：2003.1

  Reactions of Sallyl systems (allyl sulphides of RSallyl type, where R=Et, allyl, Ph, Me3C, Ph3C, as well as of allyl phenyl sulphoxide, allyl phenyl sulphone, 2,5-dihydro-1,1-dioxothiophene) with [RuClH(CO)(PPh3)3] and other ruthenium compounds have been investigated. Double-bond migration was observed in the case of allyl trityl sulphide, allyl t-butyl sulphide and both sulphones, that is, where

  的反应小号allyl系统（RSallyl类型的烯丙基硫化物，其中R =的Et，烯丙基中，Ph中，Me 3 C，博士3 C，以及烯丙基苯基砜，烯丙基苯基砜，2,5-研究了带有[RuClH（CO）（PPh 3）3 ]的二氢-1,1-二氧代噻吩）和其他钌化合物。在烯丙基三苯甲基硫醚，烯丙基叔丁基硫醚和两种砜中都观察到双键迁移，也就是说，硫的配位性能不太强。高，得到（合成的ë） -和（Ž）-RSCHCHCH 3（R =我3 C，ž：È= 96:4且Ph 3 C，ž：È = 92：8），（ê）PhS（O 2）CHCHCH 3和从各自的烯丙基系统2,3-二氢-1,1- dioxothiophene被描述。分离了烯丙基苯硫醚与[RuClH（CO）（PPh 3）3 ]的模型反应中形成的双核Ru配合物，并已解析其结构。之间的反应的机理小号allyl系统和[RuClH（CO（PPH 3）3，提出]。
• PROCESS OF PREPARING CONJUGATES OF ALLIUM ORGANOSULFUR COMPOUNDS WITH AMINO ACIDS, PEPTIDES, AND PROTEINS
  申请人：Parkin Kirk L.

  公开号：US20110082282A1

  公开（公告）日：2011-04-07

  Processes using Allium tissue homogenates and extracts in a simple and cost-effective manner to maximize the yields and recovery of thiosulfinates from Allium tissues and related organisms possessing alliinase, LF synthase and/or S-alk(en)yl-L-cysteine sulfoxides are disclosed.

  本发明揭示了使用Allium组织匀浆和提取物的过程，以简单且经济有效的方式最大化从Allium组织和相关生物中具有alliinase、LF合成酶和/或S-烷基-L-半胱氨酸亚砜的硫代磺酸盐的产量和回收率。
• Process of preparing conjugates of allium organosulfur compounds with amino acids, peptides, and proteins
  申请人：Parkin Kirk L.

  公开号：US08481284B2

  公开（公告）日：2013-07-09

  Processes using Allium tissue homogenates and extracts in a simple and cost-effective manner to maximize the yields and recovery of thiosulfinates from Allium tissues and related organisms possessing alliinase, LF synthase and/or S-alk(en)yl-L-cysteine sulfoxides are disclosed.

  本发明揭示了一种使用Allium组织匀浆和提取物以简单和经济的方式最大化从具有alliinase、LF合成酶和/或S-烷基-L-半胱氨酸亚磺酸的Allium组织和相关生物中回收硫代磺酸盐的产量和回收率的过程。
• <i>S</i>-Alk(en)ylmercaptocysteine: Chemical Synthesis, Biological Activities, and Redox-Related Mechanism
  作者：Guodong Zhang、Kirk L. Parkin

  DOI：10.1021/jf305486q

  日期：2013.2.27

  S-Alk(en)ylmercaptocysteine (CySSR, R = methyl, ethyl, propyl, 1-propenyl, and ally!), which are the putative metabolites of Allium thiosulfinates, were chemically synthesized. CySSR, but not the corresponding monosulfide species S-alk(en)yl cysteine (CySR), were able to induce quinone reductase (QR, a representative phase II enzyme) in Hepa 1c1c7 cells and inhibit nitric oxide (NO, an inflammatory biomarker) formation in lipopolysaccharide (LPS)-activated RAW 264.7 cells. These results indicate the importance of the disulfide bond for the biological activities of CySSR. Glutathione (GSH) and N-acetylcysteine (NAC), but not other types of cellular antioxidants, suppressed multiple biological activities of CySSR in vitro. The inhibitory effects of GSH and NAC on the biological activities of CySSR were correlated with a glutaredoxin (Grx)-dependent intracellular reduction of CySSR to generate cysteine and RSH, which were secreted into the extracellular medium.
• Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides
  作者：Douglas W. McMillen、Norbert Varga、Beth Ann Reed、Claudia King

  DOI：10.1021/jo991842n

  日期：2000.4.1

  The asymmetric copper-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl sulfides (2a-i) were reacted with ethyl diazoacetate in the presence of copper triflate (CuOTf) and a C-2-symmetric bis-oxazoline ligand (5a-c). The degree of asymmetric induction ranged from 2.8% for allyl methyl sulfide (2a) to 60% for (1S,2S,5R)-(+)-allyl menthyl sulfide (2d). The enantioselectivity of the reactions was also dependent on the electronic nature of the sulfide; allyl phenyl sulfide (2e) gave a 14% ee, whereas allyl p-methoxyphenyl sulfide (2i) produced only an 8% ee. The stereochemistry of 2d and (1R,2S,5R)-(+)-allyl menthyl sulfide (7) was assigned on the basis of NMR spectroscopic experiments.

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