methanesulfonic acid 3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-propyl ester | 916502-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methanesulfonic acid 3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-propyl ester
• 英文别名: 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl methanesulfonate；3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propyl methanesulfonate
• CAS: 916502-54-0
• 化学式: C₉H₁₈O₅S
• 分子量: 238.305
• InChiKey: KWLHBKKEWKFOJE-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-propyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以1.18 g的产率得到(S)-4-(3-azidopropyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  The formal synthesis of isofebrifugine using stereoselective intramolecular Michael addition

  摘要：

  The formal synthesis of isofebrifugine, a bioactive alkaloid, was achieved via a stereoselective intramolecular Michael addition reaction from D-mannitol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.021
• 作为产物：
  描述：

  3-[(4S)-2,2-二甲基-1,3-二氧戊烷-4-基]-丙醇 、 甲基磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methanesulfonic acid 3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-propyl ester
  参考文献：
  名称：

  The formal synthesis of isofebrifugine using stereoselective intramolecular Michael addition

  摘要：

  The formal synthesis of isofebrifugine, a bioactive alkaloid, was achieved via a stereoselective intramolecular Michael addition reaction from D-mannitol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.021

文献信息

• Intercalating Nucleic Acids Containing Insertions of Naphthalimide
  作者：Michael C. Wamberg、Krzysztof Walczak、Lars Andersen、Allam A. Hassan、Erik B. Pedersen

  DOI：10.1002/hlca.200690177

  日期：2006.9

  In a study of linker-length dependence, we evaluated naphthalimide (= 1H-benzo[de]isoquinoline-1,3(2H)-dione) and 4-bromonaphthalimide as intercalating nucleic acids. We used a vicinal dihydroxy system when incorporating the six different naphthalimide monomers into DNA, and found the minimum linker-length to be five C-atoms. With this length of the linker, naphthalimide was discriminating between

  在对接头长度依赖性的研究中，我们评估了萘二甲酰亚胺（= 1 H-苯并[ de ]异喹啉-1,3（2 H）-二酮）和4-溴萘二甲酰亚胺作为插入核酸。当将六种不同的萘二甲酰亚胺单体掺入DNA时，我们使用了邻位二羟基系统，发现最小的连接子长度为5个C原子。有了这样长的接头，萘二甲酰亚胺可以区分DNA和RNA-稳定DNA，同时稳定RNA。此外，萘二甲酰亚胺通过与窄至1.4°范围内的四个天然碱基杂交而显示出通用的碱基特征。当与compared比较时，具有相同连接子长度的萘二甲酰亚胺与DNA杂交时，其热解链明显更高。
• Intercalating nucleic acids (INAs) containing insertions of 6H-indolo[2,3-b]quinoxaline
  作者：Michael C. Wamberg、Allam A. Hassan、Andrew D. Bond、Erik B. Pedersen

  DOI：10.1016/j.tet.2006.09.017

  日期：2006.11

  6H-Indolo[2,3-b]quinoxaline was studied as a covalently bound heteroaromatic intercalator. Six monomers were synthesized and incorporated into DNA oligonucleotides. Through a study of linker length dependence it was concluded that the linker between the oligo and the intercalator must consist of at least five C atoms in order to stabilize a DNA duplex. An intercalator with a 2 '-deoxy-D-riboside linker to the oligo could also stabilize a DNA/RNA duplex, while (S)-4-(6-methylindolo[2,3-b]quinoxalin-3-ylmethoxy)-butane-1,2-diol was able to stabilize both DNA/DNA, DNA/RNA and a DNA/LNA duplex. Mismatch studies revealed a huge sensitivity to the C-C mismatch at the 5'-site of the intercalator. (c) 2006 Elsevier Ltd. All rights reserved.