2-lithio-4,5-dihydro-5-methyl-1,3,5-dithiazine | 61764-06-5

• 英文名称: 2-lithio-4,5-dihydro-5-methyl-1,3,5-dithiazine
• 英文别名: 4,5-Dihydro-2-lithio-5-methyl-1,3,5-dithiazin；5-methyl-1,3,5-dithiazin-2-yllithium；lithio N-methyl-thioformaldine
• CAS: 61764-06-5
• 化学式: C₄H₈LiNS₂
• 分子量: 141.187
• InChiKey: LZDSUODLFJEOKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-lithio-4,5-dihydro-5-methyl-1,3,5-dithiazine 在 碘 作用下， 以 四氢呋喃 为溶剂， 生成 bis[5-methyl[1,3,5]dithiazin-2-yl]
  参考文献：
  名称：

  Mono- and di-alkyl-[1,3,5]-dithiazinanes and their N–borane adducts revisited. Structural and theoretical study

  摘要：

  Structural analyses of a series of 5-alkyl-[1,3,5]-dithiazinanes [R = Me (1), iPr (2), tBu (3)], their N-BH3 adducts (1BH(3)-3BH(3)) and their 2-alkyl (R') derivatives are reported: R = Me, R' = Me (7); R = Me, R' iPr (8); R = iPr, R' = Me (10); R = tBu, R' = Me (11); and R = Me, R' = nBu (12). The reaction of 2-lithium-5-methyl-[1,3,5]-dithiazinane (4) with I-2 affords the bis-(5-methyl-[1,3,5]-dithiazinan-2-yl) (13). Isostructural compounds: [2,5,5]-trimethyl-[1,3,5]-dithiazinan-5-ium iodide (14), 5-borane-2,5-dimethyl-[1,3,5]-dithiazinane (15) and 2,5,5-trimethyl[1,3,5,6]-dithiazaborata (16) are compared. Structures of 7,8 and 10-13 were determined by B-11, C-13 and H-1 NMR and the X-ray diffraction analyses of 2, 1BH(3), 13 and 14 are reported. Optimization of two chair conformers of heterocycles 1-3,1BH(3)-3BH(3), 7, 9 (R = Me, R' = tBu), 13-16 were performed by HF/6-31++G and B3LYP/6-31G(d,p) methods and their minimum energy is compared. 2-Alkyl substituents or N-BH3 anchor the [1,3,5]-dithiazinane ring conformation allowing the analyses of steric and electronic interactions as well as the lone pairs effect in these molecules. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.04.021
• 作为产物：
  描述：

  二氢-5-甲基-4H-1,3,5-二噻嗪 在 正丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.0h， 生成 2-lithio-4,5-dihydro-5-methyl-1,3,5-dithiazine
  参考文献：
  名称：

  Paulsen, Hans; Stubbe, Mathias; Heiker, Fred R., Liebigs Annalen der Chemie, 1980, # 6, p. 825 - 837

  摘要：

  DOI：
• 作为试剂：
  描述：

  溴代环己烷 在 2-lithio-4,5-dihydro-5-methyl-1,3,5-dithiazine 作用下， 生成 环己烯
  参考文献：
  名称：

  Paulsen, Hans; Stubbe, Mathias; Heiker, Fred R., Liebigs Annalen der Chemie, 1980, # 6, p. 825 - 837

  摘要：

  DOI：

文献信息

• Stereocontrolled synthesis of substituted 2-alkoxytetrahydropyrans from meso-2,4-dimethylglutaric anhydride
  作者：David M. Walba、Michael D. Wand

  DOI：10.1016/s0040-4039(00)85555-0

  日期：1982.1

  Methods for efficient synthesis of A-ring fragments present in monensin and several of the nigericin group of ionophores and of α-multistriatin are described.

  描述了有效合成存在于莫能菌素中的A环环片段以及离子载体和α-多striatin中的尼日利亚黑素组中的几种的方法。
• Raubenheimer, Helgard G.; Kruger, Gert J.; Lombard, Antonie Van A., Organometallics, 1985, vol. 4, # 2, p. 275 - 284
  作者：Raubenheimer, Helgard G.、Kruger, Gert J.、Lombard, Antonie Van A.、Linford, Lorna、Viljoen, Joey C.

  DOI：——

  日期：——
• A New Lithium 5‐Methyl‐1,3‐dithia‐5‐azacyclohex‐2‐ylborate —5‐Borane and Two Dimeric 5‐Methyl‐1,3‐dithia‐5‐azacyclohex‐2‐yllithium Compounds — Stereochemistry and Reactivity
  作者：Carlos Guadarrama‐Pérez、Gregorio Cadenas‐Pliego、Luz Maria R. Martínez‐Aguilera、Angelina Flores‐Parra

  DOI：10.1002/cber.19971300622

  日期：1997.6

  AbstractSyntheses of the dimers of axial 5‐methyl‐2‐dithiazinyllithium (4) and equatorial 5‐methyl‐2‐diethiazinyllithium‐5‐borane (5), and lithium 5‐methyl‐2‐dithiazinanylborate‐5‐borane (6) are reported. Compounds 4, 5, and 6 are configurationally and conformationally stable. The 1H‐, 13H‐, 13C‐, 11B‐, and 7Li‐NMR study of th reactions of 4 and 5 with BH3S(CH3)2, BH3—THF, and CH3I is presented.
• Raubenheimer, Helgard G.; Lotz, Simon; Voljoen, Johanna, Journal of Chemical Research - Part S
  作者：Raubenheimer, Helgard G.、Lotz, Simon、Voljoen, Johanna、Plessis, Ernestus du

  DOI：——

  日期：——
• REDLICH, HARTMUT;LENFERS, JAN BERND, LIEBIGS ANN. CHEM.,(1988) N 6, 597-598
  作者：REDLICH, HARTMUT、LENFERS, JAN BERND

  DOI：——

  日期：——