endo-2-chloro-5-norbornene | 3721-18-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: endo-2-chloro-5-norbornene
• 英文别名: endo-5-chloro-2-norbornene；endo-5-chloronorbornene；(+/-)-5endo-chloro-norborn-2-ene；(+/-)-5endo-Chlor-norborn-2-en；5-endo-Chlor-norbornen-(2)；5-exo-Chlornorbornen-(2)；(1S,4S,5S)-5-chlorobicyclo[2.2.1]hept-2-ene
• CAS: 3721-18-4；3721-19-5；4313-36-4
• 化学式: C₇H₉Cl
• 分子量: 128.601
• InChiKey: PSCJIEZOAFAQRM-XVMARJQXSA-N

物化性质

• 沸点：
  174.2±9.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  endo-2-chloro-5-norbornene 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 双氧水 作用下， 生成 endo-5-chloro-exo-3-norbornanol
  参考文献：
  名称：

  Werstiuk, Nick Henry; Timmins, George; Cappelli, Frank Peter, Canadian Journal of Chemistry, 1980, vol. 58, p. 1709 - 1724

  摘要：

  DOI：
• 作为产物：
  描述：

  O-(endo-5-norbornen-2-yl)isouronium methanesulfonate 在 sodium hypochlorite 、 lithium chloride 作用下， 以 水 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 0.5h， 生成 endo-2-chloro-5-norbornene
  参考文献：
  名称：

  内向进入Nortricyclyl-Norbornenyl阳离子体系的内源：内--5-Norbornenyl-2-oxychlorocarbene的碎片化中的立体化学

  摘要：

  （碎裂小号） -内型-5-降冰片烯-2- oxychlorocarbene [（小号） - 8 ]在环己烷d 12给出〜20％（小号） -内型-2-氯-5-降冰片烯[（小号） - 7 ee约50％，ee≥95％的65-70％（R）-exo -2-氯-5-降冰片烯[（R）-4 ]和ee约12％的（R）-3-nortricyclyl chloride [[ R ] -4 ] （R）-5 ]，ee约为22％。（从对映体卡宾（R）-8开始也获得了类似的立体化学结果。）（S）-8至（S）-7和（S）-8至（R）-4转换分别主要归因于保留和反转S N i过渡态。这些已经通过计算方法定位，并且几乎是等能量的。在极性更大的溶剂（CDCl 3和CD 3 CN）中，（S）-8的碎裂越来越多地通过竞争性离子对途径发生，其中立体选择性降低，并逃逸到降冰片烯基-北三环基阳离子中，从而使产物远离内消旋-2-氯-5-降

  DOI：

  10.1021/jo051222o

文献信息

• Some Chlorine Derivatives of Norbornane (Bicyclo[2.2.1]heptane)
  作者：John D. Roberts、Frederick O. Johnson、Rudolph A. Carboni

  DOI：10.1021/ja01651a027

  日期：1954.11

  The endo-cis and trans-5,6-dichloronorbornenes were prepared by the respective additions of cis- and trans-dichlorocthylene to cyclopentadiene. The sterochemical assigments were confirmed by dipole moment studies. The cis-dichloride was inert to hydrolysis while the trans isomer was hydrolyzed to 3,5-dihydroxynortricyclene. Hydrogenation of the dichloride isomers gave the endo-cis- and trans-2,3-dichloronorbornanes

  内顺式和反式 5,6-二氯降冰片烯是通过将顺式和反式二氯乙烯分别加入环戊二烯来制备的。通过偶极矩研究证实了立体化学分配。顺式二氯化物对水解呈惰性，而反式异构体水解为 3,5-二羟基降三环烯。二氯化物异构体的氢化得到内-顺-和反-2,3-二氯降冰片烷。与基于卤化氢优先反式消除的预期相反，饱和的顺式二氯化物似乎比反式异构体更不容易脱卤化氢，尽管在两种情况下反应都很慢。两种异构体产生相同的脱卤化氢产物，2-氯降冰片烯，其结构通过氧化为顺式-环戊烷-1,3-二羧酸和水解为降樟脑而得到证实。降冰片烯在 - 75o 下氯化得到降三环基氯和 syn-7-exo-2-dichloronorbornane。由于化合物对脱卤化氢试剂的相对惰性，后者的结构被指定（优先于外-顺-2,3-二氯降冰片烷）。内-顺-2,3-二氯降冰片烷不容易水解，但反式-2,3-二氯降冰片烷和syn-7-exo-2-二氯降冰片烷分别水
• Further Investigation of the Solvolytic Reactivity of Nortricyclyl, Dehydronorbornyl and Norbornyl Halides¹
  作者：John D. Roberts、W. Bennett

  DOI：10.1021/ja01647a041

  日期：1954.9

  In a previous paper, we reported solvolytic reactivities in 80% ethanol-20% water (by volume) of nortricyclyl (I), endo-dehydronorbornyl (II), exo-dehydronorbornyl (III), endo-norbornyl (IV) and exo-norbornyl (V) halides. In subsequent publications, it was shown that the ratios of the reactivities of the exo-compounds II and IV to those of the exo-compounds III and V are much greater with the p-br

  在之前的一篇论文中，我们报道了在 80% 乙醇和 20% 水（按体积计）中的溶剂分解反应性：降三环基 (I)、内-脱氢降冰片基 (II)、外-脱氢降冰片基 (III)、内-降冰片基 (IV) 和外-降冰片基 (V) 卤化物。在随后的出版物中，表明外型化合物 II 和 IV 与外型化合物 III 和 V 的反应性比对溴苯磺酸盐的反应活性比报告的相应卤化物大得多。
• Intakes of Selected Nutrients and Food Groups and Risk of Ovarian Cancer
  作者：Susan E. McCann、Kirsten B. Moysich、Curtis Mettlin

  DOI：10.1207/s15327914nc391_3

  日期：2001.1

  In a hospital-based case-control study, we examined dietary intakes of selected nutrients and food groups and ovarian cancer risk among 496 women with primary, histologically confirmed epithelial ovarian cancer and 1,425 women with nonneoplastic diagnoses, ages 20-87 years, admitted to Roswell Park Cancer Institute between 1982 and 1998. Data on diet and other relevant risk factors in the few years before admission were collected with a se administered questionnaire. Odds ratios (OR) and 95% confidence intervals (CI) were estimated by unconditional logistic regression adjusting for age, education, region of residence, regularity of menstruation, family. history of ovarian cancer, parity, age at menarche, oral contraceptive use, and energy intake. Women in the highest vs. the lowest quartile of total energy had a weak increase in risk (OR = 1.25, 95% CI = 0.90-1.73). Significantly reduced risks were associated with higher intakes of dietary fiber (OR = 0.57, 95% CI = 0.38-0.87), vitamin A (OR = 0.66, 95% CI = 0.45-0.98), carotenoid (OR = 0.64, 95% CI = 0.43-0.93), vitamin E (OR = 0.58, 95% CI = 0.38-0.88), beta -carotene (OR = 0.68, 95% CI = 0.46-0.98), and total fruit and vegetable intake (OR = 0.62, 95% CI = 0.42-0.92). Our findings suggest that a diet high in plant foods may be important in reducing risk of ovarian cancer.
• Cis-exo addition of isothiocyanic acid to norbornenes. Synthesis and isomeric configuration of the herbicide norea
  作者：William R. Diveley、George A. Buntin、Arthur D. Lohr

  DOI：10.1021/jo01255a029

  日期：1969.3
• Moss, Robert A.; Ma, Yan; Sauers, Ronald R., Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3628 - 3634
  作者：Moss, Robert A.、Ma, Yan、Sauers, Ronald R.、Madni, Mahvash

  DOI：——

  日期：——