[(2Z)-3,7-dimethylocta-2,6-dienyl] 2,2,2-trichloroethanimidate | 852461-40-6

• 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: [(2Z)-3,7-dimethylocta-2,6-dienyl] 2,2,2-trichloroethanimidate
• CAS: 852461-40-6
• 化学式: C₁₂H₁₈Cl₃NO
• 分子量: 298.64
• InChiKey: RILLNXNDXDGILZ-CCGUKCLOSA-N

物化性质

• 沸点：
  302.2±52.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(2Z)-3,7-dimethylocta-2,6-dienyl] 2,2,2-trichloroethanimidate 在 ammonium hydroxide 、 氟化铵 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 25.0h， 生成 [(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl] [(2Z)-3,7-dimethylocta-2,6-dienyl] hydrogen phosphate
  参考文献：
  名称：

  Stereoselective synthesis of farnesylphosphoryl β-d-arabinofuranose

  摘要：

  Decaprenylphosphoryl beta-D-arabinofuranose (DPA) is a key arabinose donor in mycobacteria. In an effort to establish a practical synthetic scheme for DPA, the synthesis of nerylphosphoryl and farnesylphosphoryl beta-D-arabinofuranoses has been developed. The products were obtained by coupling of a suitably protected P-D-arabinofuranosyl phosphate intermediate with activated forms of the C-10 nerol and C-15 trans,trans-farnesol and subsequent deprotection. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.151
• 作为产物：
  描述：

  橙花醇 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 [(2Z)-3,7-dimethylocta-2,6-dienyl] 2,2,2-trichloroethanimidate
  参考文献：
  名称：

  Stereoselective synthesis of farnesylphosphoryl β-d-arabinofuranose

  摘要：

  Decaprenylphosphoryl beta-D-arabinofuranose (DPA) is a key arabinose donor in mycobacteria. In an effort to establish a practical synthetic scheme for DPA, the synthesis of nerylphosphoryl and farnesylphosphoryl beta-D-arabinofuranoses has been developed. The products were obtained by coupling of a suitably protected P-D-arabinofuranosyl phosphate intermediate with activated forms of the C-10 nerol and C-15 trans,trans-farnesol and subsequent deprotection. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.151

文献信息

• Alkylation of thiols with trichloroacetimidates under neutral conditions
  作者：Brian C. Duffy、Kyle T. Howard、John D. Chisholm

  DOI：10.1016/j.tetlet.2014.12.042

  日期：2015.6

  Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates
  作者：Maju Joe、Todd L. Lowary

  DOI：10.1016/j.carres.2006.08.020

  日期：2006.11

  Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl P-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Stereoselectivity in the synthesis of polyprenylphosphoryl β-d-ribofuranoses
  作者：Avraham Liav、Ewa Swiezewska、Ewa Ciepichal、Patrick J. Brennan

  DOI：10.1016/j.tetlet.2006.09.163

  日期：2006.12

  Decaprenylphosphoryl beta-D-arabinofuranose (DPA) is a key arabinose donor in mycobacteria. The ribo analog of DPA (DPR) has also been found in mycobacteria. It has recently been confirmed that DPA is formed via a two-step epimerization of DPR. The stereoselective synthesis of DPR as well as two shorter analogs of DPR is described. (c) 2006 Elsevier Ltd. All rights reserved.