2-[(5-Chlorofuran-2-yl)methyl]-5,5-dimethyl-1,3,2lambda5-dioxaphosphinane 2-oxide | 279669-05-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-[(5-Chlorofuran-2-yl)methyl]-5,5-dimethyl-1,3,2lambda5-dioxaphosphinane 2-oxide
• 英文别名: 2-[(5-chlorofuran-2-yl)methyl]-5,5-dimethyl-1,3,2λ5-dioxaphosphinane 2-oxide
• CAS: 279669-05-5
• 化学式: C₁₀H₁₄ClO₄P
• 分子量: 264.646
• InChiKey: NAROYUALIGEFOU-UHFFFAOYSA-N

物化性质

• 沸点：
  332.8±30.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对硝基苯甲醛 、 2-[(5-Chlorofuran-2-yl)methyl]-5,5-dimethyl-1,3,2lambda5-dioxaphosphinane 2-oxide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以99%的产率得到2-chloro-5-[(E)-2-(4-nitrophenyl)ethenyl]furan
  参考文献：
  名称：

  Chlorophosphonates:  Inexpensive Precursors for Stereodefined Chloro-Substituted Olefins and Unsymmetrical Disubstituted Acetylenes

  摘要：

  New chlorophosphonates bearing a 1,3,2-dioxaphosphorinane ring which are useful for the stereospecific synthesis of 5-chlorofurfuryl substituted olefins and chloro-substituted dienes have been obtained by an easy, inexpensive route. The utility of some of these in the synthesis of ferrocenyl- and anthracenyl-substituted unsymmetrical acetylenes has been explored. The structures of the phosphonates (OCH2CMe2CH2O)P(O)CH2(C4H2ClO) (4) and (OCH2Me2CH2O)P(O)-(CH=CHCH(Cl)Ph (7) have been determined; in addition, the stereochemistry of (5-chlorofurfuryl)-CH=CH(4-ClC6H4) (13b) and 2,4-Cl2C6H3-CH=CH-CH=C(Ph)Cl (14a) is unambiguously proved by the X-ray structure determination.

  DOI：

  10.1021/jo991946y
• 作为产物：
  描述：

  2-氯-5,5-二甲基-1,3,2-二氧磷杂环己烷 在 氯化亚砜 、 水 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 2-[(5-Chlorofuran-2-yl)methyl]-5,5-dimethyl-1,3,2lambda5-dioxaphosphinane 2-oxide
  参考文献：
  名称：

  Chlorophosphonates:  Inexpensive Precursors for Stereodefined Chloro-Substituted Olefins and Unsymmetrical Disubstituted Acetylenes

  摘要：

  New chlorophosphonates bearing a 1,3,2-dioxaphosphorinane ring which are useful for the stereospecific synthesis of 5-chlorofurfuryl substituted olefins and chloro-substituted dienes have been obtained by an easy, inexpensive route. The utility of some of these in the synthesis of ferrocenyl- and anthracenyl-substituted unsymmetrical acetylenes has been explored. The structures of the phosphonates (OCH2CMe2CH2O)P(O)CH2(C4H2ClO) (4) and (OCH2Me2CH2O)P(O)-(CH=CHCH(Cl)Ph (7) have been determined; in addition, the stereochemistry of (5-chlorofurfuryl)-CH=CH(4-ClC6H4) (13b) and 2,4-Cl2C6H3-CH=CH-CH=C(Ph)Cl (14a) is unambiguously proved by the X-ray structure determination.

  DOI：

  10.1021/jo991946y

文献信息

• Ferrocenyl substituted chlorostilbenes and butadienes
  作者：K Senthil Kumar、K.C Kumara Swamy

  DOI：10.1016/s0022-328x(01)00978-0

  日期：2001.12
• Direct synthesis of α-substituted phosphonates
  作者：K Praveen Kumar、C Muthiah、Sudha Kumaraswamy、K.C Kumara Swamy

  DOI：10.1016/s0040-4039(01)00399-9

  日期：2001.4
• Chlorophosphonates:  Inexpensive Precursors for Stereodefined Chloro-Substituted Olefins and Unsymmetrical Disubstituted Acetylenes
  作者：C. Muthiah、K. Praveen Kumar、C. Aruna Mani、K. C. Kumara Swamy

  DOI：10.1021/jo991946y

  日期：2000.6.1

  New chlorophosphonates bearing a 1,3,2-dioxaphosphorinane ring which are useful for the stereospecific synthesis of 5-chlorofurfuryl substituted olefins and chloro-substituted dienes have been obtained by an easy, inexpensive route. The utility of some of these in the synthesis of ferrocenyl- and anthracenyl-substituted unsymmetrical acetylenes has been explored. The structures of the phosphonates (OCH2CMe2CH2O)P(O)CH2(C4H2ClO) (4) and (OCH2Me2CH2O)P(O)-(CH=CHCH(Cl)Ph (7) have been determined; in addition, the stereochemistry of (5-chlorofurfuryl)-CH=CH(4-ClC6H4) (13b) and 2,4-Cl2C6H3-CH=CH-CH=C(Ph)Cl (14a) is unambiguously proved by the X-ray structure determination.