4-羟基-4-甲基-2-戊酮-d12 | 114253-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-4-甲基-2-戊酮-d12
• 中文别名: 二丙酮醇-D12；4-羟基-4-甲基-2-戊酮-D12
• 英文名称: d12-4-hydroxy-4-methyl-2-pentanone
• 英文别名: 4-hydroxy-4-methylpentan-2-one；octadeuterio-4-deuteriooxy-4-trideuteriomethyl-pentan-2-one；Octadeuterio-4-deuteriooxy-4-trideuteriomethyl-pentan-2-on；Diacetone alcohol-d12；1,1,1,3,3,5,5,5-octadeuterio-4-deuteriooxy-4-(trideuteriomethyl)pentan-2-one
• CAS: 114253-85-9
• 化学式: C₆H₁₂O₂
• 分子量: 128.065
• InChiKey: SWXVUIWOUIDPGS-YDUIPVTMSA-N

物化性质

• 沸点：
  166 °C(lit.)
• 密度：
  1.028 g/mL at 25 °C(lit.)
• 闪点：
  143 °F
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• 稳定性/保质期：

  如果按照规定使用和储存，则不会发生分解，并且没有已知的危险反应。应避免与强氧化剂、还原剂及强碱接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 储存条件：
  保持贮藏器密封，并将其存放在阴凉、干燥的地方。同时，确保工作间有良好的通风或排气装置。

反应信息

• 作为反应物：
  描述：

  4-羟基-4-甲基-2-戊酮-d12 在 对甲苯磺酸 作用下， 以 乙醚 为溶剂， 生成 2,4-dimethylpent-3-en-2-ol-1,1,1,3,5,5,5,4',4',4'-d10
  参考文献：
  名称：

  Stereochemistry in the Ene Reactions of Singlet Oxygen and Triazolinediones with Allylic Alcohols. A Mechanistic Comparison

  摘要：

  The ene reaction of singlet oxygen with (Z)-4-methylpent-3-en-2-ol-2,5,5,5-d(4) (1-OH-d4) in nonpolar solvents exhibits a 90% three diastereoselectivity in the adduct derived from the major syn perepoxide intermediate, but also a moderate three diastereoselectivity in the adduct derived from the minor anti perepoxide. Photooxygenation of 2,4-dimethylpent-3-en-2-ol (2) exhibits a significant solvent dependence in the syn/anti methyl stereoselectivity, with nonpolar solvents promoting syn methyl reactivity, while polar solvents promote anti methyl reactivity. These results are in agreement with a steering effect between hydroxyl and singlet oxygen in the rate-determining step of the reaction. N-Phenyltriazolinedione addition to the chiral allylic alcohol 4-methylpent-3-en-2-ol (1-OH) is highly three diastereoselective in nonpolar solvents, with a solvent dependent variation in the threo/erythro ene products. On the other hand, the nonfunctionalized chiral alkene 2,4-dimethyl-2-hexene (1-Et) exhibits poor diastereoselectivity. Reaction of PTAD with 1-OH-d4 in nonpolar solvents, exhibits a significant three diastereoselectivity from the syn aziridinium imide intermediate, and a moderate three diastereoselectivity from the anti intermediate. These results are consonant with a steering effect between the hydroxyl and the electrophile, as proposed in the case of singlet oxygen addition to allylic alcohols 1-OH and 2. In contrast to the analogous O-1(2) ene reaction, a solvent independent ratio syn/anti similar to 50/50 was found in the addition of MTAD to 2. The intermolecular kinetic isotope effect in the reaction of 2 with MTAD (k(H)/k(D) = 1.15 +/- 0.02), is consistent with formation of the intermediate in fast step, indicative that the steering effect during the formation of aziridium imide is not important in the reaction kinetics. This energetic profile is in contrast to triazolinedione addition to the secondary allylic alcohol 1-OH, where the high three selectivity and the slight inverse kinetic isotope effect of k(H)/k(D) = 0.98 +/- 0.02 are consonant with the formation of the intermediate in the rate-determining step. An explanation for the increased reactivity of the syn methyl in the addition of MTAD to 2 (similar to 50%) is offered.

  DOI：

  10.1021/jo990258b
• 作为产物：
  描述：

  氘代丙酮 生成 4-羟基-4-甲基-2-戊酮-d12
  参考文献：
  名称：

  三唑啉二酮与手性烯丙基醇的非对映选择性烯反应。亲羟基分子转向作用的证据

  摘要：

  PTAD与手性烯丙醇4-甲基-3-戊烯-2-醇的烯反应在非极性溶剂中表现出高的苏非对映选择性，而在极性溶剂中，非对映选择性显着降低。根据非对映异构体顺式和反叠氮基亚胺中间体的形成过程中羟基与传入的亲油体之间的导向作用来讨论这些结果。

  DOI：

  10.1016/s0040-4039(98)00207-x

文献信息

• Silicon-Directed Oxa-Pictet−Spengler Cyclization and an Unusual Dimerization of 2-Trimethylsilanyl Tryptophols
  作者：Xuqing Zhang、Xiaojie Li、James C. Lanter、Zhihua Sui

  DOI：10.1021/ol050623n

  日期：2005.5.1

  The tetrahydro-pyrano[3,4-b]indoles 6 were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)-ethanols 5 and various ketones or aldehydes through silicon-directed oxa-Pictet-Spengler cyclizations. An unusual reaction led to the dimeric products 7 when some of 5 was treated with acetone using BF(3) as the catalyst.

  由2-（2-三甲基硅烷基-1H-吲哚-3-基）-乙醇5和各种酮或醛通过硅定向的oxa-Pictet-Spengler环化反应合成四氢吡喃并[3,4-b]吲哚6。当使用BF（3）作为催化剂用丙酮处理5个化合物中的一些时，一个不寻常的反应导致生成二聚产物7。
• Dinuclear Olefin and Alkyne Complexes of Platinum(II)
  作者：Anja König、Martin Bette、Clemens Bruhn、Dirk Steinborn

  DOI：10.1002/ejic.201200744

  日期：2012.12

  decomposition. Complexes 2–7 and 11/12 were isolated in pure states and fully characterized by elemental analysis, NMR spectroscopy, and X-ray diffraction measurements (2, 11, 12). For the dinuclear bis(olefin) (1–3) and bis(alkyne) complexes (11, 12) solvent-dependent equilibria between the transoid and cisoid isomers were observed, and these could even be ascertained crystallographically for complex [PtCl2(tBuC≡CtBu)}2]

  制备了 Zeise 二聚体类型的双（烯烃）配合物 - [PtCl2(cis-MeHC=CHMe)}2] (2) 或 [PtCl2(c-Hex)}2] (3, c-Hex = 环己烯) -通过在 SnCl2 或 K[PtCl3(cis-MeHC=CHMe)] 存在下用相应的烯烃处理 K2[PtCl4]。发现 Zeise 的二聚体 [PtCl2(H2C=CH2)}2] (1) 在氯仿或二氯甲烷中与内部炔烃 RC≡CtBu (R = Me, tBu) 反应，前提是去除了裂解的乙烯, 以产生 Zeise 二聚体类型的双 (炔) 复合物 [PtCl2(RC≡CtBu)}2] (R = Me, 11; tBu, 12)。在不去除乙烯的情况下，单核混合乙烯/炔配合物顺式-[PtCl2(H2C= )(RC≡CtBu)] (R = Me, 8; tBu, 9) 和顺式-[PtCl2(H2C= )2]
• Pocker, Chemistry and industry, 1959, p. 89
  作者：Pocker

  DOI：——

  日期：——