(1R,1'R)-3-exo,3'-exo-bithiocamphor | 156198-31-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,1'R)-3-exo,3'-exo-bithiocamphor
• 英文别名: (1R,3S,4R)-1,7,7-trimethyl-3-[(1R,2S,4R)-4,7,7-trimethyl-3-sulfanylidene-2-bicyclo[2.2.1]heptanyl]bicyclo[2.2.1]heptane-2-thione
• CAS: 156198-31-1
• 化学式: C₂₀H₃₀S₂
• 分子量: 334.59
• InChiKey: LPOAGIYGFYCXJD-JWRMFUQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,1'R)-3-exo,3'-exo-bithiocamphor 在 ruthenium trichloride 、 sodium periodate 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.05h， 生成 (1R,1'R)-3-exo,3'-exo-Bicamphor
  参考文献：
  名称：

  Bithiocamphor: an interesting synthon for the synthesis of chiral ligands

  摘要：

  Bithiocamphor 1 was studied; its reduction led to dithiols 3a and 3b, its oxidation led to bicamphor 8.

  DOI：

  10.1016/0957-4166(96)00039-0
• 作为产物：
  描述：

  (1R)-(-)-硫代樟脑 在 potassium tert-butylate 、 碘 作用下， 以 异丙醇 为溶剂， 反应 7.5h， 生成 (1R,1'R)-3-exo,3'-exo-bithiocamphor
  参考文献：
  名称：

  Bithiocamphor: an interesting synthon for the synthesis of chiral ligands

  摘要：

  Bithiocamphor 1 was studied; its reduction led to dithiols 3a and 3b, its oxidation led to bicamphor 8.

  DOI：

  10.1016/0957-4166(96)00039-0

文献信息

• 3-exo,3′-exo-(1R,1′R)-Bithiocamphor — a versatile source for functionally different 3,3′-bibornane derivatives — I. Ring-closure reactions and prototropic rearrangements
  作者：Werner Schroth、Ekkehard Hintzsche、Roland Spitzner、Dieter Ströhl、Joachim Sieler

  DOI：10.1016/0040-4020(95)00852-y

  日期：1995.11

  The title compound 3, derived from (+)-camphor, allows preparatively useful conversions to be carried out at the 3,3′-bibornane skeleton. The reactions are characterized by steric factors. Despite the increasing steric strain in the bicyclic units, ring-closure reactions of 3 to born-2-ene anellated sulfur-heterocycles are possible, including the formation of the 1,2-dithiine (6), thiophene (11), and

  衍生自（+）-樟脑的标题化合物3允许在3,3'-联萘烷烷骨架上进行制备上有用的转化。反应以空间因素为特征。尽管双环单元中的空间应变增加，但3到生成的2烯代芳族硫杂环的闭环反应还是可能的，包括形成1,2-二硫氨酸（6），噻吩（11）和1分别是，2，3-三硫平系统（13）。化合物6的特点是具有几种不同的性质。与脂肪族硫酮的正常行为相反，3不能作为烯醇存在。后者和相关中间体可通过1,5-质子重排立即稳定，从而导致冰片亚烷基单元，例如16个及以上的产品。
• 3-exo,3′-exo-(1R,1′R)-Bithiocamphor — a versatile source for functionally different 3,3′-bibornane derivatives, II. 1 An access to 3-exo,3′-exo-(1r,1′r)-bicamphor and related compounds
  作者：Werner Schroth、Ekkehard Hintzsche、Roland Spitzner、Dieter Ströhl、Katrin Schmeiβ、Joachim Sieler

  DOI：10.1016/0040-4020(95)00849-4

  日期：1995.11

  3-exo,3′-exo-(1R,1′R)-bicamphor (12) is obtained from 3-exo,3′-exo-(1R,1′R)-bithtiocamphor (3) by condensation with hydrazine hydrate followed by hydrolysis of the resulting dihydropyridazine 11. Deprotonation of 12 with NaH and subsequent treatment with potassium hexacyanoferrate (III) furnishes the 2,2′-dioxo-3,3′-bibornanylidene 13, whilst reduction of 12 with L1AlH4 affords the 3,3′-biisoborneol

  3-外型，3'-外切- （1 - [R，1' - [R）-bicamphor（12）从3-获得外，3'-外切- （1 - [R，1' - [R）-bithtiocamphor（3）通过缩合水合肼，然后水解生成的二氢哒嗪11。用NaH脱除12的质子，然后用六氰合铁酸钾（III）处理，得到2,2'-dioxo-3,3'-bibornanylidene 13，而用L1AlH 4还原12则得到3,3'-bi异冰片16。描述了对各种2,2'-双官能3,3'-联萘烷衍生物的进一步相关转化，作为手性配体可能是令人感兴趣的
• (1R,1′R)-di-born-2-eno[2,3-c;3′,2′-e][1,2]dithiin, ein cyclisches disulfid mit ungewöhnlichen eigenschaften
  作者：Werner Schroth、Ekkehard Hintzsche、Roland Spitzner、Hermann Irngartinger、Volker Siemund

  DOI：10.1016/s0040-4039(00)73025-5

  日期：1994.3

  The title compound 8, obtained by oxidation of bis-thiocamphor 6, represents a kinetically stabilized disulfide. Despite deeply colored, as usual in the 1,2-dithiine series, 8 displays various other features in strict contrast to the normal behaviour of 1,2-dithiines. Thus, 8 prefers S-insertion to the 1,2,3-trithiepine 14 instead of S-extrusion to the thiophene 12. Furthermore, ring opening by nucleophilic reagents is followed by 1,5-H-shifts leading to blue enthiones, e.g. 17, 18, and 19.
• Single step first synthesis of a 3,6-dihydro-1,2-dithiin from its parent 1,4-dithioketone via a stereospecific rearrangement
  作者：Paul Salama、Marc Poirier

  DOI：10.1016/s0957-4166(97)00279-6

  日期：1997.8

  The one step conversion of bis-thiocamphor into its corresponding 3,6-dihydro-1,2-dithiin was performed via a stereospecific rearrangement. Proof of the reaction stereospecificity was established by full characterization of the final product. Some speculative mechanistic avenues are exposed. (C) 1997 Elsevier Science Ltd.
• Bithiocamphor: an interesting synthon for the synthesis of chiral ligands
  作者：Murielle Bonnat、Jean-Olivier Durand、Maurice Le Corre

  DOI：10.1016/0957-4166(96)00039-0

  日期：1996.2

  Bithiocamphor 1 was studied; its reduction led to dithiols 3a and 3b, its oxidation led to bicamphor 8.