4-(1,3-dithiolan-2-yl)butan-1-ol | 57795-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 4-(1,3-dithiolan-2-yl)butan-1-ol
• 英文别名: 1,3-dithiolane-2-butanol；4-[1,3]dithiolan-2-yl-butan-1-ol；2-(4-Hydroxybutyl)-1,3-dithiolan
• CAS: 57795-09-2
• 化学式: C₇H₁₄OS₂
• 分子量: 178.32
• InChiKey: DTSCDUKMNOOOCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  119 °C(Press: 0.5 Torr)
• 密度：
  1.168 g/cm3(Temp: 23 °C)

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：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1,3-dithiolan-2-yl)butan-1-ol 在 氨 、 calcium 作用下， 生成 8-Hydroxy-3-thia-1-octan-thiol
  参考文献：
  名称：

  Martin,M.; Bassery,L., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1975, vol. 280, p. 1529 - 1532

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-dihydro-3-nitro-4-<(tetrahydro-2H-pyran-2-yl)oxy>isoxazole 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 1.84h， 生成 4-(1,3-dithiolan-2-yl)butan-1-ol
  参考文献：
  名称：

  2-Amino-2-deoxytetrose Derivatives. Preparation from 4,5-Dihydroisoxazoles via Reductive Cleavage

  摘要：

  The 4-alkoxy-3-nitro-4,5-dihydroisoxazoles 2a,b were prepared by condensation of nitromethane and chloroacetaldehyde, protection of the resulting nitroaldol Ic, and subsequent nitrosative cyclization. Multistep replacement of the nitro group of 2a,b by a 2-(1,3-dithiolanyl) group gave 7a,b. Reaction of 7b with lithium borohydride afforded reductive cleavage of the dihydroisoxazole ring to produce the open-chain diastereomeric amino alcohols 6a,b. A reproducible ratio of > 90: 10 6a/6b was obtained using freshly prepared hydride reagent. The amino alcohols were converted to the corresponding (R*,R*)-amide 6c and (R*,S*)-amide 6d which were chromatographically separated. The(R*,R*)-amide was transformed into the 2-amino-2-deoxythreose derivatives 11a,b and hence to 12 while the (R*,S*)-amide was similarly transformed to 2-amino-2-deoxyerythrose derivative 14a and its anomeric isomer 14b.

  DOI：

  10.1021/jo00125a015

文献信息

• A removable functional group in a photochemical macrocyclic synthesis
  作者：Masao Wada、Hideo Nakai、Yasuhiko Sato、Yasumaru Hatanaka、Yuichi Kanaoka

  DOI：10.1016/s0040-4020(01)91979-9

  日期：——

  Based on a regioselective remote photocyclization of a pair system consisting of a phthalimide group and a dithiolanyl group, a variety of aza-cyclic compounds with methylene, ester, or amide groups in their frameworks were synthesized. The dithiolanyl group provides a removable donor, which effects a needed reaction followed by removal to give a new carbon skeleton leaving little trace of the precursor

  基于由邻苯二甲酰亚胺基和二硫杂环戊烷基组成的对系统的区域选择性远程光环化，合成了在其骨架中具有亚甲基，酯或酰胺基的各种氮杂环化合物。二硫杂环戊烷基提供了可去除的供体，其影响了所需的反应，随后被去除以提供新的碳骨架，几乎没有痕量的前体形式。
• Wada, Masao; Nakai, Hideo; Sato, Yasuhiko, Chemical and pharmaceutical bulletin, 1982, vol. 30, p. 3414 - 3417
  作者：Wada, Masao、Nakai, Hideo、Sato, Yasuhiko、Kanaoka, Yuichi

  DOI：——

  日期：——
• WADA, MASAO;NAKAI, HIDEO;SATO, YASUHIKO;KANAOKA, YUICHI, CHEM. AND PHARM. BULL., 1982, 30, N 9, 3414-3417
  作者：WADA, MASAO、NAKAI, HIDEO、SATO, YASUHIKO、KANAOKA, YUICHI

  DOI：——

  日期：——
• WADA, MASAO;NAKAI, HIDEO;SATO, YASUHIKO;HATANAKA, YASUMARU;KANAOKA, YUICH+, TETRAHEDRON, 1983, 39, N 16, 2691-2698
  作者：WADA, MASAO、NAKAI, HIDEO、SATO, YASUHIKO、HATANAKA, YASUMARU、KANAOKA, YUICH+

  DOI：——

  日期：——
• MARTIN M.; BASSERY L., C. R. ACAD. SCI. <CHDC-AQ>, 1975, T. 280, NO 25, 1529-1532
  作者：MARTIN M.、 BASSERY L.

  DOI：——

  日期：——